Rhodium-catalyzed C–H functionalization of heteroarenes using indoleBX hypervalent iodine reagents

Erwann Grenet,
Ashis Das,
Paola Caramenti and
Jérôme Waser

Letter
Published 25 May 2018

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1. Graphical Abstract
2. Figure 1: Bioactive compounds with pyridinone, quinolone and indole cores.
  
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3. Scheme 1: C–H functionalization of pyridinones and quinoline N-oxides.
  
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4. Scheme 2: Scope and limitations of the Rh-catalyzed C–H activation of [1,2'-bipyridin]-2-one.
  
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5. Scheme 3: Scope of the Rh-catalyzed peri C–H activation of quinoline N-oxides.
  
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6. Scheme 4: Product modifications.
  
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Beilstein J. Org. Chem. 2018, 14, 1208–1214, doi:10.3762/bjoc.14.102

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Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent

Elsa Deruer,
Vincent Hamel,
Samuel Blais and
Sylvain Canesi

Letter
Published 24 May 2018

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1. Graphical Abstract
2. Scheme 1: Mechanistic hypothesis.
  
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3. Scheme 2: Extension of the method.
  
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4. Scheme 3: Carbon-based nucleophiles.
  
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5. Scheme 4: THF ring opening.
  
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Beilstein J. Org. Chem. 2018, 14, 1203–1207, doi:10.3762/bjoc.14.101

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Stereoselective nucleophilic addition reactions to cyclic N-acyliminium ions using the indirect cation pool method: Elucidation of stereoselectivity by spectroscopic conformational analysis and DFT calculations

Koichi Mitsudo,
Junya Yamamoto,
Tomoya Akagi,
Atsuhiro Yamashita,
Masahiro Haisa,
Kazuki Yoshioka,
Hiroki Mandai,
Koji Ueoka,
Christian Hempel,
Jun-ichi Yoshida and
Seiji Suga

Letter
Published 24 May 2018

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1. Graphical Abstract
2. Scheme 1: Generation and reaction of cationic species generated by “indirect cation pool” methods.
  
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3. Figure 1: (a) ¹H NMR of N-acyliminium ion C1 in CD₂Cl₂ at −80 °C (600 MHz). (b) Preferred conformation of C1.
  
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4. Figure 2: (a) ¹H NMR spectrum of C3 in CD₂Cl₂ at −60 °C (400 MHz). (b) Preferred conformation of C3.
  
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5. Figure 3: (a) ¹H NMR spectrum of C5 in CD₂Cl₂ at −60 °C (400 MHz). (b) Preferred conformation of C5.
  
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6. Figure 4: Summary of the conformations of N-acyliminium ions C1–C6.
  
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7. Figure 5: Stevens’ hypothesis on the tendency of the addition of nucleophiles to N-acyliminium ions. The subs...
  
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8. Figure 6: A plausible mechanism of the observed diastereoselective reaction of the N-acyliminium ions.
  
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9. Figure 7: Comparison of ΔG for the pseudo-equatorial and pseudo-axial conformations of C1–C6 at the B3LYP/6-3...
  
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Beilstein J. Org. Chem. 2018, 14, 1192–1202, doi:10.3762/bjoc.14.100

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Are dispersion corrections accurate outside equilibrium? A case study on benzene

Tim Gould,
Erin R. Johnson and
Sherif Abdulkader Tawfik

Full Research Paper
Published 23 May 2018

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1. Graphical Abstract
2. Figure 1: Interaction energies (solid lines) and forces (dashed lines) for the parallel configuration of the ...
  
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3. Figure 2: Interaction energies (solid lines) and forces (dashed lines) for the T configuration of the benzene...
  
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4. Figure 3: Interaction energies U(R;D) = E(R;D) − E(0;D) (solid lines) and forces (dashed lines) for the slipp...
  
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5. Figure 4: SCAN and SCAN+rVV10 results for the Parallel (top left) and T (top right) configurations of the ben...
  
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Beilstein J. Org. Chem. 2018, 14, 1181–1191, doi:10.3762/bjoc.14.99

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One hundred years of benzotropone chemistry

Arif Dastan,
Haydar Kilic and
Nurullah Saracoglu

Review
Published 23 May 2018

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1. Graphical Abstract
2. Scheme 1: Tropone (1), tropolone (2) and their resonance structures.
  
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3. Figure 1: Natural products containing a tropone nucleus.
  
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4. Figure 2: Possible isomers 11–13 of benzotropone.
  
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5. Scheme 2: Synthesis of benzotropones 11 and 12.
  
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6. Scheme 3: Oxidation products of benzotropylium fluoroborate (16).
  
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7. Scheme 4: Oxidation of 7-bromo-5H-benzo[7]annulene (22).
  
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8. Scheme 5: Synthesis of 4,5-benzotropone (11) using o-phthalaldehyde (27).
  
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9. Scheme 6: Synthesis of 4,5-benzotropone (11) starting from oxobenzonorbornadiene 31.
  
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10. Scheme 7: Acid-catalyzed cleavage of oxo-bridge of 34.
  
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11. Scheme 8: Synthesis of 4,5-benzotropone (11) from o-xylylene dibromide (38).
  
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12. Scheme 9: Synthesis of 4,5-benzotropone (11) via the carbene adduct 41.
  
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13. Scheme 10: Heck coupling strategy for the synthesis of 11.
  
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14. Scheme 11: Synthesis of benzofulvalenes via carbonyl group of 4,5-benzotropone (11).
  
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15. Figure 3: Some cycloheptatrienylium cations.
  
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16. Scheme 12: Synthesis of condensation product 63 and its subsequent oxidative cyclization products.
  
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17. Figure 4: A novel series of benzo[7]annulenes prepared from 4,5-benzotropone (11).
  
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18. Scheme 13: Preparation of substituted benzo[7]annulene 72 using the Mukaiyama-Michael reaction.
  
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19. Figure 5: Possible benzo[7]annulenylidenes 73–75.
  
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20. Scheme 14: Thermal and photochemical decomposition of 7-diazo-7H-benzo[7]annulene (76) and the trapping of int...
  
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21. Scheme 15: Synthesis of benzoheptafulvalene 86.
  
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22. Scheme 16: Synthesis of 7-(diphenylmethylene)-7H-benzo[7]annulene (89).
  
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23. Scheme 17: Reaction of 4,5-benzotropone (11) with dimethyl diazomethane.
  
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24. Scheme 18: Synthesis of dihydrobenzomethoxyazocine 103.
  
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25. Scheme 19: Synthesis and reducibility of benzo-homo-2-methoxyazocines.
  
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26. Scheme 20: Synthesis of 4,5-benzohomotropones 104 and 115 from 4,5-benzotropones 11 and 113.
  
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27. Scheme 21: A catalytic deuterogenation of 4,5-benzotropone (11) and synthesis of 5-monosubstituted benzo[7]ann...
  
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28. Scheme 22: Synthesis of methyl benzo[7]annulenes 131 and 132.
  
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29. Scheme 23: Ambident reactivity of halobenzo[7]annulenylium cations 133a/b.
  
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30. Scheme 24: Preparation of benzo[7]annulenylidene–iron complexes 147.
  
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31. Scheme 25: Synthesis of 1-ethynylbenzotropone (150) and the etheric compound 152 from 4,5-benzotropone (11) wi...
  
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32. Scheme 26: Thermal decomposition of 4,5-benzotropone (11).
  
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33. Scheme 27: Reaction of 4,5-benzotropone (11) with 1,2-ethanediol and 1,2-ethanedithiol.
  
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34. Scheme 28: Conversions of 1-benzosuberone (162) to 2,3-benzotropone (12).
  
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35. Scheme 29: Synthesis strategies for 2,3-bezotropone (12) using 1-benzosuberones.
  
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36. Scheme 30: Oxidation-based synthesis of 2,3-benzotropone (12) via 1-benzosuberone (162).
  
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37. Scheme 31: Synthesis of 2,3-benzotropone (12) from α-tetralone (171) via ring-expansion.
  
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38. Scheme 32: Preparation of 2,3-benzotropone (12) by using of benzotropolone 174.
  
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39. Figure 6: Benzoheptafulvenes as condensation products of 2,3-benzotropone (12).
  
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40. Scheme 33: Conversion of 2,3-benzotropone (12) to tosylhydrazone salt 182 and gem-dichloride 187.
  
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41. Figure 7: Benzohomoazocines 191–193 and benzoazocines 194–197.
  
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42. Scheme 34: From 2,3-benzotropone (12) to carbonium ions 198–201.
  
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43. Scheme 35: Cycloaddition reactions of 2,3-benzotropone (12).
  
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44. Scheme 36: Reaction of 2,3-benzotropone (12) with various reagents and compounds.
  
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45. Figure 8: 3,4-Benzotropone (13) and its resonance structure.
  
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46. Scheme 37: Synthesis of 6,7-benzobicyclo[3.2.0]hepta-3,6-dien-2-one (230).
  
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47. Figure 9: Photolysis and thermolysis products of 230.
  
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48. Figure 10: Benzotropolones and their tautomeric structures.
  
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49. Scheme 38: Synthesis strategies of 4,5-benzotropolone (238).
  
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50. Scheme 39: Synthesis protocol for 2-hydroxy-4,5-benzotropone (238) using oxazole-benzo[7]annulene 247.
  
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51. Figure 11: Some quinoxaline and pyrazine derivatives 254–256 prepared from 4,5-benzotropolone (238).
  
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52. Scheme 40: Nitration product of 4,5-benzotropolone (238) and its isomerization to 1-nitro-naphthoic acid (259)....
  
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53. Scheme 41: Synthesis protocol for 6-hydroxy-2,3-benzotropone (239) from benzosuberone (162).
  
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54. Scheme 42: Various reactions via 6-hydroxy-2,3-benzotropone (239).
  
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55. Scheme 43: Photoreaction of 6-hydroxy-2,3-benzotropone (239).
  
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56. Scheme 44: Synthesis of 7-hydroxy-2,3-benzotropone (241) from benzosuberone (162).
  
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57. Scheme 45: Synthesis strategy for 7-hydroxy-2,3-benzotropone (241) from ketone 276.
  
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58. Scheme 46: Synthesis of 7-hydroxy-2,3-benzotropone (241) from β-naphthoquinone (280).
  
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59. Scheme 47: Synthesis of 7-hydroxy-2,3-benzotropone (241) from bicyclic endoperoxide 213.
  
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60. Scheme 48: Synthesis of 7-hydroxy-2,3-benzotropone (241) by ring-closing metathesis.
  
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61. Figure 12: Various monosubstitution products 289–291 of 7-hydroxy-2,3-benzotropone (241).
  
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62. Scheme 49: Reaction of 7-hydroxy-2,3-benzotropone (241) with various reagents.
  
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63. Scheme 50: Synthesis of 4-hydroxy-2,3-benzotropones 174 and 304 from diketones 300/301.
  
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64. Scheme 51: Catalytic hydrogenation of diketones 300 and 174.
  
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65. Scheme 52: Synthesis of halo-benzotropones from alkoxy-naphthalenes 306, 307 and 310.
  
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66. Figure 13: Unexpected byproducts 313–315 during synthesis of chlorobenzotropone 309.
  
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67. Figure 14: Some halobenzotropones and their cycloadducts.
  
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68. Scheme 53: Multisep synthesis of 2-chlorobenzotropone 309.
  
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69. Scheme 54: A multistep synthesis of 2-bromo-benzotropone 26.
  
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70. Scheme 55: A multistep synthesis of bromo-2,3-benzotropones 311 and 316.
  
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71. Scheme 56: Oxidation reactions of 8-bromo-5H-benzo[7]annulene (329) with some oxidants.
  
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72. Scheme 57: Synthesis of 2-bromo-4,5-benzotropone (26).
  
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73. Scheme 58: Synthesis of 6-chloro-2,3-benzotropone (335) using LiCl and proposed intermediate 336.
  
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74. Scheme 59: Reaction of 7-bromo-2,3-benzotropone (316) with methylamine.
  
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75. Scheme 60: Reactions of bromo-2,3-benzotropones 26 and 311 with dimethylamine.
  
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76. Scheme 61: Reactions of bromobenzotropones 311 and 26 with NaOMe.
  
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77. Scheme 62: Reactions of bromobenzotropones 26 and 312 with t-BuOK in the presence of DPIBF.
  
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78. Scheme 63: Cobalt-catalyzed reductive cross-couplings of 7-bromo-2,3-benzotropone (316) with cyclic α-bromo en...
  
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79. Figure 15: Cycloadduct 357 and its di-π-methane rearrangement product 358.
  
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80. Scheme 64: Catalytic hydrogenation of 2-chloro-4,5-benzotropone (311).
  
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81. Scheme 65: Synthesis of dibromo-benzotropones from benzotropones.
  
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82. Scheme 66: Bromination/dehydrobromination of benzosuberone (162).
  
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83. Scheme 67: Some transformations of isomeric dibromo-benzotropones 261A/B.
  
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84. Scheme 68: Transformations of benzotropolone 239B to halobenzotropolones 369–371.
  
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85. Figure 16: Bromobenzotropolones 372–376 and 290 prepared via bromination/dehydrobromination strategy.
  
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86. Scheme 69: Synthesis of some halobenzotropolones 289, 377 and 378.
  
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87. Figure 17: Bromo-chloro-derivatives 379–381 prepared via chlorination.
  
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88. Scheme 70: Synthesis of 7-iodo-3,4-benzotropolone (382).
  
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89. Scheme 71: Hydrogenation of bromobenzotropolones 369 and 370.
  
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90. Scheme 72: Debromination reactions of mono- and dibromides 290 and 375.
  
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91. Figure 18: Nitratation and oxidation products of some halobenzotropolenes.
  
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92. Scheme 73: Azo-coupling reactions of some halobenzotropolones 294, 375 and 378.
  
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93. Figure 19: Four possible isomers of dibenzotropones 396–399.
  
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94. Figure 20: Resonance structures of tribenzotropone (400).
  
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95. Scheme 74: Two synthetic pathways for tribenzotropone (400).
  
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96. Scheme 75: Synthesis of tribenzotropone (400) from dibenzotropone 399.
  
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97. Scheme 76: Synthesis of tribenzotropone (400) from 9,10-phenanthraquinone (406).
  
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98. Scheme 77: Synthesis of tribenzotropone (400) from trifluoromethyl-substituted arene 411.
  
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99. Figure 21: Dibenzosuberone (414).
  
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100. Figure 22: Reduction products 415 and 416 of tribenzotropone (400).
  
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101. Figure 23: Structures of tribenzotropone dimethyl ketal 417 and 4-phenylfluorenone (412) and proposed intermed...
  
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102. Figure 24: Structures of benzylidene- and methylene-9H-tribenzo[a,c,e][7]annulenes 419 and 420 and chiral phos...
  
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103. Figure 25: Structures of tetracyclic alcohol 422, p-quinone methide 423 and cation 424.
  
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104. Figure 26: Structures of host molecules 425–427.
  
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105. Scheme 78: Synthesis of non-helical overcrowded derivatives syn/anti-431.
  
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106. Figure 27: Hexabenzooctalene 432.
  
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107. Figure 28: Structures of possible eight isomers 433–440 of naphthotropone.
  
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108. Scheme 79: Synthesis of naphthotropone 437 starting from 1-phenylcycloheptene (441).
  
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109. Scheme 80: Synthesis of 10-hydroxy-11H-cyclohepta[a]naphthalen-11-one (448) from diester 445.
  
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110. Scheme 81: Synthesis of naphthotropone 433.
  
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111. Scheme 82: Synthesis of naphthotropones 433 and 434 via cycloaddition reaction.
  
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112. Scheme 83: Synthesis of naphthotropone 434 starting from 452.
  
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113. Figure 29: Structures of tricarbonyl(tropone)irons 458, and possible cycloadducts 459.
  
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114. Scheme 84: Synthesis of naphthotropone 436.
  
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115. Scheme 85: Synthesis of precursor 465 for naphthotropone 435.
  
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116. Scheme 86: Generation of naphthotropone 435 from 465.
  
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117. Figure 30: Structures of tropylium cations 469 and 470.
  
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118. Figure 31: Structures of tropylium ions 471^+.BF₄⁻, 472^+.BF₄⁻, and 473^+.BF₄⁻.
  
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119. Scheme 87: Synthesis of tropylium ions 471^+.BF₄⁻ and 479^+.ClO₄⁻.
  
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120. Scheme 88: Synthesis of 1- and 2-methylanthracene (481 and 482) via carbene–carbene rearrangement.
  
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121. Figure 32: Trapping products 488–490.
  
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122. Scheme 89: Generation and chemistry of a naphthoannelated cycloheptatrienylidene-cycloheptatetraene intermedia...
  
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123. Scheme 90: Proposed intermediates and reaction pathways for adduct 498.
  
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124. Scheme 91: Exited-state intramolecular proton transfer of 505.
  
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125. Figure 33: Benzoditropones 506 and 507.
  
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126. Scheme 92: Synthesis of benzoditropone 506e.
  
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127. Scheme 93: Synthetic approaches for dibenzotropone 507 via tropone (1).
  
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128. Scheme 94: Formation mechanisms of benzoditropone 507 and 516 via 515.
  
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129. Scheme 95: Synthesis of benzoditropones 525 and 526 from pyromellitic dianhydride (527).
  
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130. Figure 34: Possible three benzocyclobutatropones 534–536.
  
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131. Scheme 96: Synthesis of benzocyclobutatropones 534 and 539.
  
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132. Scheme 97: Synthesis attempts for benzocyclobutatropone 545.
  
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133. Scheme 98: Generation and trapping of symmetric benzocyclobutatropone 536.
  
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134. Scheme 99: Synthesis of chloro-benzocyclobutatropone 552 and proposed mechanism of fluorenone derivatives.
  
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135. Scheme 100: Synthesis of tropolone analogue 559.
  
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136. Scheme 101: Synthesis of tropolones 561 and 562.
  
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137. Figure 35: o/p-Tropoquinone rings (563 and 564) and benzotropoquinones (565–567).
  
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138. Scheme 102: Synthesis of benzotropoquinone 566.
  
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139. Scheme 103: Synthesis of benzotropoquinone 567 via a Diels–Alder reaction.
  
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140. Figure 36: Products 575–577 through 1,2,3-benzotropoquinone hydrate 569.
  
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141. Scheme 104: Structures 578–582 prepared from tropoquinone 567.
  
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142. Figure 37: Two possible structures 583 and 584 for dibenzotropoquinone, and precursor compound 585 for 583.
  
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143. Scheme 105: Synthesis of saddle-shaped ketone 592 using dibenzotropoquinone 584.
  
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Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

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Recyclable hypervalent-iodine-mediated solid-phase peptide synthesis and cyclic peptide synthesis

Dan Liu,
Ya-Li Guo,
Jin Qu and
Chi Zhang

Full Research Paper
Published 22 May 2018

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1. Graphical Abstract
2. Figure 1: Iodosodilactone and FPID.
  
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3. Scheme 1: Proposed mechanism for FPID-mediated amide bond formation.
  
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4. Scheme 2: Solid-phase peptide synthesis mediated by FPID/(4-MeOC₆H₄)₃P. Conditions: The resin loading for 2-C...
  
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5. Scheme 3: The regeneration of FPID after SPPS.
  
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6. Figure 2: Structure of pseudostellarin D.
  
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7. Scheme 4: Synthetic strategies of pseudostellarin D.
  
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8. Scheme 5: Preparation of the precursor of pseudostellarin D.
  
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Beilstein J. Org. Chem. 2018, 14, 1112–1119, doi:10.3762/bjoc.14.97

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Iodine(III)-mediated halogenations of acyclic monoterpenoids

Laure Peilleron,
Tatyana D. Grayfer,
Joëlle Dubois,
Robert H. Dodd and
Kevin Cariou

Full Research Paper
Published 18 May 2018

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1. Graphical Abstract
2. Figure 1: Halogenated terpenoids from natural sources.
  
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3. Scheme 1: Previously developed bromo-functionalizations of polyprenoids using iodine(III) reagents.
  
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4. Figure 2: Selected monoterpenoids used in this study.
  
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5. Scheme 2: Dibromination of acyclic monoterpenoids.
  
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6. Scheme 3: Bromo(trifluoro)acetoxylation of acyclic monoterpenoids.
  
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7. Scheme 4: Bromohydroxylation of acyclic monoterpenoids.
  
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8. Scheme 5: Iodo(trifluoro)acetoxylation of acyclic monoterpenoids.
  
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9. Scheme 6: Chlorination of acyclic monoterpenoids.
  
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10. Scheme 7: General mechanism proposal for the formation of 2–6 and control experiments.
  
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Beilstein J. Org. Chem. 2018, 14, 1103–1111, doi:10.3762/bjoc.14.96

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Synthetic avenues towards a tetrasaccharide related to Streptococcus pneumonia of serotype 6A

Aritra Chaudhury,
Mana Mohan Mukherjee and
Rina Ghosh

Full Research Paper
Published 17 May 2018

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1. Graphical Abstract
2. Figure 1: The tetrasaccharides associated with the pneumonicoccal serogroup 6.
  
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3. Figure 2: Retrosynthetic analysis.
  
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4. Scheme 1: Preparation of D-glucosyl donor 6. Reaction conditions: a) NapBr/PMBCl, NaH, DMF, rt, 12 h, 90% (6a...
  
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5. Scheme 2: Preparation of L-rhamnosyl acceptor 5. Reaction conditions: a) Py, BzCl, rt, 12 h, 99%; b) DDQ, DCM...
  
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6. Scheme 3: Preparation of ribitol acceptor 7. Reaction conditions: a) Me₂C(OMe)₂, pTSA, CH₃COCH₃, rt, 81%; b) ...
  
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7. Scheme 4: Stepwise synthesis of tetrasaccharide 1. Reaction conditions: a) TMSOTf, DCM/Et₂O (5:1), 4 Å MS, −3...
  
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8. Scheme 5: One-pot synthesis of tetrasaccharide 1. Reaction conditions: a) TMSOTf, 4 Å MS, DCM/Et₂O (4:1), N₂,...
  
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Beilstein J. Org. Chem. 2018, 14, 1095–1102, doi:10.3762/bjoc.14.95

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Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system

Toshifumi Dohi,
Shohei Ueda,
Kosuke Iwasaki,
Yusuke Tsunoda,
Koji Morimoto and
Yasuyuki Kita

Letter
Published 16 May 2018

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1. Graphical Abstract
2. Scheme 1: Hypervalent iodine(III)-induced benzylic C–H functionalization for oxidative coupling with carboxyl...
  
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3. Scheme 2: Radical reactivities of the I(III)–Br bond generated from PIDA.
  
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4. Scheme 3: Benzylic C–H carboxylations by the iodosobenzene/NaBr system.
  
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5. Scheme 4: Outline of the proposed reaction mechanism for the PIDA/NaBr system.
  
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6. Scheme 5: Reaction of benzyl bromide 2h’ under radical C–H acetoxylation conditions.
  
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Beilstein J. Org. Chem. 2018, 14, 1087–1094, doi:10.3762/bjoc.14.94

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An overview of recent advances in duplex DNA recognition by small molecules

Sayantan Bhaduri,
Nihar Ranjan and
Dev P. Arya

Review
Published 16 May 2018

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1. Graphical Abstract
2. Figure 1: A figure showing the hydrogen bonding patterns observed in (a) duplex (b) triplex and (c) quadruple...
  
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3. Figure 2: (a) Portions of MATα1–MATα2 are shown contacting the minor groove of the DNA substrate. Key arginin...
  
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4. Figure 3: Chemical structures of naturally occurring and synthetic hybrid minor groove binders.
  
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5. Figure 4: Synthetic structural analogs of distamycin A by replacing one or more pyrrole rings with other hete...
  
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6. Figure 5: Pictorial representation of the binding model of pyrrole–imidazole (Py/Im) polyamides based on the ...
  
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7. Figure 6: Chemical structures of synthetic “hairpin” pyrrole–imidazole (Py/Im) conjugates.
  
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8. Figure 7: (a) Minor groove complex formation between DNA duplex and 8-ring cyclic Py/Im polyamide (conjugate ...
  
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9. Figure 8: Telomere-targeting tandem hairpin Py/Im polyamides 23 and 24 capable of recognizing >10 base pairs; ...
  
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10. Figure 9: Representative examples of recently developed DNA minor groove binders.
  
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11. Figure 10: Chemical structures of bisbenzamidazoles Hoechst 33258 and 33342 and their synthetic structural ana...
  
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12. Figure 11: Chemical structures of bisamidines such as diminazene, DAPI, pentamidine and their synthetic struct...
  
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13. Figure 12: Representative examples of recently developed bisamidine derivatives.
  
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14. Figure 13: Chemical structures of chromomycin, mithramycin and their synthetic structural analogs 91 and 92.
  
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15. Figure 14: Chemical structures of well-known naturally occurring DNA binding intercalators.
  
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16. Figure 15: Naturally occurring indolocarbazole rebeccamycin and its synthetic analogs.
  
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17. Figure 16: Representative examples of naturally occurring and synthetic derivatives of DNA intercalating agent...
  
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18. Figure 17: Several recent synthetic varieties of DNA intercalators.
  
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19. Figure 18: Aminoglycoside (neomycin)–Hoechst 33258/intercalator conjugates.
  
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20. Figure 19: Chemical structures of triazole linked neomycin dimers and neomycin–bisbenzimidazole conjugates.
  
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21. Figure 20: Representative examples of naturally occurring and synthetic analogs of DNA binding alkylating agen...
  
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22. Figure 21: Chemical structures of naturally occurring and synthetic analogs of pyrrolobenzodiazepines.
  
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Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

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Hypervalent iodine(III)-mediated decarboxylative acetoxylation at tertiary and benzylic carbon centers

Kensuke Kiyokawa,
Daichi Okumatsu and
Satoshi Minakata

Full Research Paper
Published 15 May 2018

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1. Graphical Abstract
2. Scheme 1: Decarboxylative functionalization using PhI(OAc)₂/I₂ system.
  
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3. Scheme 2: Substrate scope. Reactions were conducted on a 0.5 mmol scale at a 0.2 or 0.4 M concentration on th...
  
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4. Scheme 3: Hydrolysis of acetates.
  
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5. Scheme 4: Mechanistic investigations.
  
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6. Scheme 5: Proposed reaction pathway.
  
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Beilstein J. Org. Chem. 2018, 14, 1046–1050, doi:10.3762/bjoc.14.92

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Hypervalent iodine-guided electrophilic substitution: para-selective substitution across aryl iodonium compounds with benzyl groups

Cyrus Mowdawalla,
Faiz Ahmed,
Tian Li,
Kiet Pham,
Loma Dave,
Grace Kim and
I. F. Dempsey Hyatt

Full Research Paper
Published 14 May 2018

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1. Graphical Abstract
2. Scheme 1: Examples of the reductive iodonio-Claisen rearrangement compared to new reactivity seen with benzyl...
  
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3. Scheme 2: Crossover reaction experiments.
  
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4. Scheme 3: Suggested mechanism based on product formation and crossover experiments.
  
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5. Scheme 4: Proposed mechanism for the generation of 2i from Table 2, entry 8.
  
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Beilstein J. Org. Chem. 2018, 14, 1039–1045, doi:10.3762/bjoc.14.91

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Imide arylation with aryl(TMP)iodonium tosylates

Souradeep Basu,
Alexander H. Sandtorv and
David R. Stuart

Letter
Published 11 May 2018

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1. Graphical Abstract
2. Scheme 1: Imides as an important scaffold.
  
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3. Scheme 2: Scope of compatible aryl groups. Conditions: 1 (0.5 mmol, 1 equiv), potassium phthalimide (2.5 mmol...
  
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4. Scheme 3: One-pot synthesis of anilines.
  
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Beilstein J. Org. Chem. 2018, 14, 1034–1038, doi:10.3762/bjoc.14.90

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Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores

Sang Won Park,
Soong-Hyun Kim,
Jaeyoung Song,
Ga Young Park,
Darong Kim,
Tae-Gyu Nam and
Ki Bum Hong

Letter
Published 11 May 2018

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1. Graphical Abstract
2. Scheme 1: Hypervalent iodine-mediated heterofunctionalization of terminal alkenes.
  
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3. Scheme 2: Substrate scope of the Ritter-type oxyamidation: isoxazoline synthesis. All reactions were performe...
  
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4. Scheme 3: Substrate scope of Ritter-type amido-amidation: pyrazoline synthesis. All reactions were performed ...
  
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5. Scheme 4: Plausible mechanism of the hypervalent iodine(III)-mediated Ritter-type oxyamidation/amido-amidatio...
  
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Beilstein J. Org. Chem. 2018, 14, 1028–1033, doi:10.3762/bjoc.14.89

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Fluorocyclisation via I(I)/I(III) catalysis: a concise route to fluorinated oxazolines

Felix Scheidt,
Christian Thiehoff,
Gülay Yilmaz,
Stephanie Meyer,
Constantin G. Daniliuc,
Gerald Kehr and
Ryan Gilmour

Full Research Paper
Published 09 May 2018

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1. Graphical Abstract
2. Figure 1: Selected examples of bioactive compounds containing the 2-oxazoline motif.
  
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3. Figure 2: The catalytic difluorination of alkenes (top) and the proposed fluorocyclisation via the same I(I)/...
  
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4. Figure 3: Substrate scope. ^aReaction conducted on 1 mmol scale. ^bReaction time increased to 40 hours. ^cReacti...
  
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5. Scheme 1: Exploring diastereocontrol and the synthesis of the fluorohydrin 3. Yields in parentheses were dete...
  
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6. Figure 4: X-ray molecular structure of compound 2c. Thermal ellipsoids shown at the 50% propability level. To...
  
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Beilstein J. Org. Chem. 2018, 14, 1021–1027, doi:10.3762/bjoc.14.88

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Preparation, structure, and reactivity of bicyclic benziodazole: a new hypervalent iodine heterocycle

Akira Yoshimura,
Michael T. Shea,
Cody L. Makitalo,
Melissa E. Jarvi,
Gregory T. Rohde,
Akio Saito,
Mekhman S. Yusubov and
Viktor V. Zhdankin

Full Research Paper
Published 08 May 2018

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1. Graphical Abstract
2. Scheme 1: Representative examples of benziodoxoles and benziodazoles.
  
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3. Scheme 2: Preparation of bicyclic benziodazole 7a.
  
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4. Figure 1: X-ray crystal structure of compound 7a. Ellipsoids are drawn to the 50% probability level. Selected...
  
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5. Scheme 3: Benziodadiazole 7a mediated oxidatively assisted esterification and amidation reactions.
  
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Beilstein J. Org. Chem. 2018, 14, 1016–1020, doi:10.3762/bjoc.14.87

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Polysubstituted ferrocenes as tunable redox mediators

Sven D. Waniek,
Jan Klett,
Christoph Förster and
Katja Heinze

Full Research Paper
Published 07 May 2018

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1. Graphical Abstract
2. Scheme 1: Selected transformations with ferrocene/ferrocenium as SET reagents (a) [27], catalyzed (b,c) [29-31] and medi...
  
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3. Scheme 2: Methyl esters of ferrocene carboxylic acids 1 [45,46], 2 [47-49], 2a [50], 2b [51,52], 3, 4 [54] and pseudo octahedral high-spin...
  
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4. Figure 1: Normalized cyclic voltammograms for anodic sweeps of 1–4 in CH₂Cl₂/[n-Bu₄N][B(C₆F₅)₄] (scan rate 10...
  
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5. Figure 2: Electrochemical potentials E_1/2 (vs FcH/FcH⁺) of esters 1–4 versus sum of Hammett values ∑σ_p/m with...
  
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6. Figure 3: a) Partial ATR IR spectra (transmission normalized, C=O stretching vibration region) of solids 1–4....
  
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7. Figure 4: IR spectroelectrochemical oxidation of 3 to 3⁺ in CH₂Cl₂/[n-Bu₄N][B(C₆F₅)₄] (C=O stretching vibrati...
  
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8. Figure 5: a) Normalized UV–vis spectra of 1–4 in CH₂Cl₂. b) Normalized UV–vis absorptions of 1⁺–4⁺ in CH₂Cl₂/[...
  
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9. Figure 6: Absorption energy E of ferrocene bands of 1–4 (a) and energies of the low energy absorption maxima ...
  
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10. Figure 7: UV–vis spectroelectrochemical oxidation of 3 in CH₂Cl₂/[n-Bu₄N][B(C₆F₅)₄] (0–1.1 V vs Ag pseudo ref...
  
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11. Figure 8: ¹H NMR oxidation titration of 3 in CD₂Cl₂ with [N(2,4-C₆H₃Br₂)₃]⁺ as oxidant. ^a[N(2,4-C₆H₃Br₂)₃]. ^b...
  
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Beilstein J. Org. Chem. 2018, 14, 1004–1015, doi:10.3762/bjoc.14.86

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The first Pd-catalyzed Buchwald–Hartwig aminations at C-2 or C-4 in the estrone series

Ildikó Bacsa,
Dávid Szemerédi,
János Wölfling,
Gyula Schneider,
Lilla Fekete and
Erzsébet Mernyák

Full Research Paper
Published 04 May 2018

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1. Graphical Abstract
2. Scheme 1: Pd-catalyzed aminations at C-2 or C-4 in the 13α-estrone series. Reactions were performed on a 0.25...
  
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3. Scheme 2: Two-step synthesis of 2-amino-13α-estra-1,3,5(10)-trien-17-one (13).
  
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Beilstein J. Org. Chem. 2018, 14, 998–1003, doi:10.3762/bjoc.14.85

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Cross-coupling of dissimilar ketone enolates via enolonium species to afford non-symmetrical 1,4-diketones

Keshaba N. Parida,
Gulab K. Pathe,
Shimon Maksymenko and
Alex M. Szpilman

Full Research Paper
Published 03 May 2018

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1. Graphical Abstract
2. Scheme 1: Oxidative intermolecular cross-coupling of dissimilar enolates.
  
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3. Scheme 2: Scope of the homo- and heterocoupling of enolates. The purple bond indicates the bond formed. The b...
  
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4. Scheme 3: Study of diastereoselectivity of the cross-coupling reaction.
  
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Beilstein J. Org. Chem. 2018, 14, 992–997, doi:10.3762/bjoc.14.84

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Correlation effects and many-body interactions in water clusters

Andreas Heßelmann

Full Research Paper
Published 02 May 2018

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1. Graphical Abstract
2. Figure 1: Number of two-body, three-body and four-body clusters for systems with up to 13 molecules.
  
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3. Figure 2: Water clusters from [23] studied in this work.
  
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4. Figure 3: Cyclic-chair structure of the water hexamer.
  
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5. Figure 4: Comparison of the structures of the first seven water clusters optimized on the Hartree–Fock and MP...
  
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6. Figure 5: Electrostatic and dispersion interaction energy for three different structures of the water dimer. ...
  
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7. Figure 6: Two- and three-body dispersion energies for three structures of the water trimer. In all conformati...
  
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8. Figure 7: Number of three-body subclusters for which the three-body dispersion energy is attractive (red) or ...
  
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9. Figure 8: DFT-SAPT energy decomposition of the three-body interaction energy of the water trimer calculated u...
  
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10. Figure 9: DFT-SAPT energy decomposition of the sum of the three- and four-body interaction energy of the wate...
  
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11. Figure 10: Sum of three- and four-body dispersion interactions compared to the total many-body interactions Δ³...
  
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12. Figure 11: Relative contribution of the two-body dispersion interaction energy to the complete two-body and to...
  
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Beilstein J. Org. Chem. 2018, 14, 979–991, doi:10.3762/bjoc.14.83

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2-Iodo-N-isopropyl-5-methoxybenzamide as a highly reactive and environmentally benign catalyst for alcohol oxidation

Takayuki Yakura,
Tomoya Fujiwara,
Akihiro Yamada and
Hisanori Nambu

Full Research Paper
Published 30 Apr 2018

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1. Graphical Abstract
2. Figure 1: Structures of pentavalent iodine oxidants 1 and 2, and iodine catalysts 3–13.
  
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3. Figure 2: Structures of the catalysts 16–25.
  
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4. Scheme 1: Oxidation of the monovalent iodine derivatives 17 and 3 to the pentavalent iodine derivatives 29 an...
  
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5. Figure 3: Reaction profile of the oxidation of (a) iodobenzamide 17 and (b) 2-iodobenzoic acid (3) with Oxone^®...
  
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6. Scheme 2: Plausible reaction mechanism for the oxidation of alcohols catalyzed by the 2-iodobenzamides.
  
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Beilstein J. Org. Chem. 2018, 14, 971–978, doi:10.3762/bjoc.14.82

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Mechanochemistry of nucleosides, nucleotides and related materials

Olga Eguaogie,
Joseph S. Vyle,
Patrick F. Conlon,
Manuela A. Gîlea and
Yipei Liang

Review
Published 27 Apr 2018

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1. Graphical Abstract
2. Figure 1: Examples of equipment used to perform mechanochemistry on nucleoside and nucleotide substrates (not...
  
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3. Figure 2: Ganciclovir.
  
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4. Scheme 1: Nucleoside tritylation effected by hand grinding in a heated mortar and pestle.
  
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5. Scheme 2: Persilylation of ribonucleoside hydroxy groups (and in situ acylation of cytidine) in a MBM.
  
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6. Scheme 3: Nucleoside amine and carboxylic acid Boc protection using an improvised attritor-type mill.
  
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7. Scheme 4: Nucleobase Boc protection via transient silylation using an improvised attritor-type mill.
  
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8. Scheme 5: Chemoselective N-acylation of an aminonucleoside using LAG in a MBM.
  
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9. Scheme 6: Azide–alkyne cycloaddition reactions performed in a copper vessel in a MBM.
  
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10. Figure 3: a) Custom-machined copper vessel and zirconia balls used to perform CuAAC reactions (showing: upper...
  
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11. Scheme 7: Thiolate displacement reactions of nucleoside derivatives in a MBM.
  
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12. Scheme 8: Selenocyanate displacement reactions of nucleoside derivatives in a MBM.
  
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13. Scheme 9: Nucleobase glycosidation reactions and subsequent deacetylation performed in a MBM.
  
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14. Scheme 10: Regioselective phosphorylation of nicotinamide riboside in a MBM.
  
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15. Scheme 11: Preparation of nucleoside phosphoramidites in a MBM using ionic liquid-stabilised chlorophosphorami...
  
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16. Scheme 12: Preparation of a nucleoside phosphite triester using LAG in a MBM.
  
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17. Scheme 13: Internucleoside phosphate coupling linkages in a MBM.
  
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18. Scheme 14: Preparation of ADPR analogues using in a MBM.
  
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19. Scheme 15: Synthesis of pyrophosphorothiolate-linked dinucleoside cap analogues in a MBM to effect hydrolytic ...
  
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20. Figure 4: Early low temperature mechanised ball mill as described by Mudd et al. – adapted from reference [78].
  
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21. Scheme 16: Co-crystal grinding of alkylated nucleobases in an amalgam mill (N.B. no frequency was recorded in ...
  
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22. Figure 5: Materials used to prepare a smectic phase.
  
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23. Figure 6: Structures of 5-fluorouracil (5FU) and nucleoside analogue prodrugs subject to mechanochemical co-c...
  
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24. Scheme 17: Preparation of DNA-SWNT complex in a MBM.
  
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Beilstein J. Org. Chem. 2018, 14, 955–970, doi:10.3762/bjoc.14.81

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On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

Eirinaios I. Vrettos,
Gábor Mező and
Andreas G. Tzakos

Review
Published 26 Apr 2018

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1. Graphical Abstract
2. Figure 1: Conventional chemotherapy versus targeted chemotherapy. Black color = Solid malignant tumor; red = ...
  
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3. Figure 2: A. General structural architecture of the ideal navigated drug delivery system [31]. B. General structu...
  
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4. Figure 3: Binding and penetration mechanism of iRGD. The iRGD peptide is accumulated on the surface of αv int...
  
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5. Figure 4: Representative examples of anticancer drugs utilized for the construction of PDCs. The most usual c...
  
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6. Figure 5: Illustration of the drug release mechanism from the self-immolative spacer PABC conjugated to a tum...
  
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7. Figure 6: Structures of the PDCs named AN-152 and AN-207.
  
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8. Figure 7: Structure of the PDC named AN-238.
  
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9. Figure 8: Chemical structure and synthetic scheme for the PDC ANG1005. (A) ANG1005 is composed of three molec...
  
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10. Figure 9: Structure of oxime linked Dau–GnRH-III conjugate with or without cathepsin B labile spacer and thei...
  
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11. Figure 10: Synthesis of the most effective GnRH-III–Dau conjugate with two drug molecules [153].
  
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12. Figure 11: Structures of the four different PDCs of D-Lys⁶-GnRH-I and gemcitabine (GSG, GSG₂, 3G, 3G₂) [19].
  
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13. Figure 12: Structures of (A) native sunitinib; (B) SAN1 analog of sunitinib and (C) assembled PDC named SAN1GS...
  
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14. Figure 13: Synthetic scheme for the formation of GSG and the unexpected side product [156].
  
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15. Figure 14: Illustration of uncharted guanidinium peptide coupling reagent side reactions during PDCs synthesis ...
  
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16. Figure 15: Putative mechanism for the formation of the uronium side product [156].
  
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Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

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Local energy decomposition analysis of hydrogen-bonded dimers within a domain-based pair natural orbital coupled cluster study

Ahmet Altun,
Frank Neese and
Giovanni Bistoni

Full Research Paper
Published 25 Apr 2018

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1. Graphical Abstract
2. Figure 1: The conformers of (a) water dimer and (b) HF dimer.
  
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3. Figure 2: Schematic representation of strong pair excitations in the framework of the DLPNO-CCSD(T) method. E...
  
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4. Figure 3: Dissociation curve of Conf1 of water dimer as a function of the H-bond distance. Its nearly linear ...
  
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5. Figure 4: Decomposed HF energy terms (top), and correlation energy terms (bottom) of Conf1 of water dimer as ...
  
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6. Figure 5: Comparison of total interaction, electrostatic interaction, and London dispersion energies calculat...
  
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Beilstein J. Org. Chem. 2018, 14, 919–929, doi:10.3762/bjoc.14.79

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Development of novel cyclic NGR peptide–daunomycin conjugates with dual targeting property

Andrea Angelo Pierluigi Tripodi,
Szilárd Tóth,
Kata Nóra Enyedi,
Gitta Schlosser,
Gergely Szakács and
Gábor Mező

Full Research Paper
Published 25 Apr 2018

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1. Graphical Abstract
2. Figure 1: Schematic synthesis of cyclic KNGRE (A) and XNGRE (B) drug conjugates. a) Mtt-cleavage: 2% TFA/DCM;...
  
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3. Figure 2: (A) HT1080 and (B) HT-29 cells. Uptake of conjugate 1 (light green); 2 (red); 3 (light blue); 4 (pi...
  
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