High-yielding continuous-flow synthesis of antimalarial drug hydroxychloroquine

Eric Yu,
Hari P. R. Mangunuru,
Nakul S. Telang,
Caleb J. Kong,
Jenson Verghese,
Stanley E. Gilliland III,
Saeed Ahmad,
Raymond N. Dominey and
B. Frank Gupton

Full Research Paper
Published 08 Mar 2018

8109 Accesses

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1. Graphical Abstract
2. Figure 1: Commercially available antimalarial drugs.
  
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3. Scheme 1: Current batch syntheses of the key intermediate 5-(ethyl(2-hydroxyethyl)amino)pentan-2-one (6).
  
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4. Scheme 2: Retrosynthetic strategy to hydroxychloroquine (1).
  
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5. Scheme 3: Schematic representation for continuous in-line extraction of 10.
  
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6. Scheme 4: Optimization of the flow process for the synthesis of 12.
  
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Beilstein J. Org. Chem. 2018, 14, 583–592, doi:10.3762/bjoc.14.45

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Correction: Mechanochemical enzymatic resolution of N-benzylated-β³-amino esters

Mario Pérez-Venegas,
Gloria Reyes-Rangel,
Adrián Neri,
Jaime Escalante and
Eusebio Juaristi

Correction
Published 12 Oct 2017

3372 Accesses

Beilstein J. Org. Chem. 2017, 13, 2128–2130, doi:10.3762/bjoc.13.210

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Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

Martina Tireli,
Silvija Maračić,
Stipe Lukin,
Marina Juribašić Kulcsár,
Dijana Žilić,
Mario Cetina,
Ivan Halasz,
Silvana Raić-Malić and
Krunoslav Užarević

Full Research Paper
Published 06 Nov 2017

2635 Accesses

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1. Graphical Abstract
2. Scheme 1: Synthetic procedures for preparation of p-halogen-substituted and non-substituted phenyl-1,2,3-tria...
  
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3. Figure 1: Experimental Raman spectra of the alkyne 4 and triazole products 5–8. Bands attributed to the vibra...
  
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4. Figure 2: In situ Raman monitoring of a) mechanochemical formation of triazole 5 using copper(II) acetate mon...
  
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5. Figure 3: a) In situ Raman monitoring for mechanochemical synthesis of 5 using brass balls and PMMA reaction ...
  
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6. Figure 4: ESR spectra of samples obtained after milling by methods 2a (black), 2b (red) and 2c (blue). The in...
  
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7. Figure 5: X-ray structure of the triazole compounds. (a) Molecular structure of 5, with the atom-numbering sc...
  
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Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

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Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione

Yan Sun,
Jing Sun and
Chao-Guo Yan

Full Research Paper
Published 03 Jan 2013

2323 Accesses

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1. Graphical Abstract
2. Scheme 1: The four-component reactions containing dimedone (a) and cyclopentane-1,3-dione (b).
  
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3. Figure 1: Molecular structure of spiro[dihydropyridine-oxindole] 1b.
  
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4. Figure 2: The two kinds of spiro compounds from reactions of isatins with arylamines and cyclic 1,3-diketones....
  
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5. Figure 3: Molecular structure of spiro[dihydropyridine-oxindole] 2f.
  
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6. Scheme 2: Condensation reactions of isatins with cyclopentane-1,3-dione.
  
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7. Figure 4: Molecular structure of compound 3d.
  
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8. Scheme 3: Proposed reaction mechanism for the three-component reaction.
  
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Beilstein J. Org. Chem. 2013, 9, 8–14, doi:10.3762/bjoc.9.2

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An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

Marcus Baumann and
Ian R. Baxendale

Review
Published 30 Oct 2013

1433 Accesses

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1. Graphical Abstract
2. Scheme 1: Scaled industrial processes for the synthesis of simple pyridines.
  
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3. Scheme 2: Synthesis of nicotinic acid from 2-methyl-5-ethylpyridine (1.11).
  
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4. Scheme 3: Synthesis of 3-picoline and nicotinic acid.
  
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5. Scheme 4: Synthesis of 3-picoline from 2-methylglutarodinitrile 1.19.
  
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6. Scheme 5: Picoline-based synthesis of clarinex (no yields reported).
  
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7. Scheme 6: Mode of action of proton-pump inhibitors and structures of the API’s.
  
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8. Scheme 7: Hantzsch-like route towards the pyridine rings in common proton pump inhibitors.
  
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9. Figure 1: Structures of rosiglitazone (1.40) and pioglitazone (1.41).
  
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10. Scheme 8: Synthesis of rosiglitazone.
  
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11. Scheme 9: Syntheses of 2-pyridones.
  
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12. Scheme 10: Synthesis and mechanism of 2-pyrone from malic acid.
  
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13. Scheme 11: Polymer-assisted synthesis of rosiglitazone.
  
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14. Scheme 12: Synthesis of pioglitazone.
  
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15. Scheme 13: Meerwein arylation reaction towards pioglitazone.
  
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16. Scheme 14: Route towards pioglitazone utilising tyrosine.
  
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17. Scheme 15: Route towards pioglitazone via Darzens ester formation.
  
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18. Scheme 16: Syntheses of the thiazolidinedione moiety.
  
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19. Scheme 17: Synthesis of etoricoxib utilising Negishi and Stille cross-coupling reactions.
  
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20. Scheme 18: Synthesis of etoricoxib via vinamidinium condensation.
  
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21. Figure 2: Structures of nalidixic acid, levofloxacin and moxifloxacin.
  
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22. Scheme 19: Synthesis of moxifloxacin.
  
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23. Scheme 20: Synthesis of (S,S)-2,8-diazabicyclo[4.3.0]nonane 1.105.
  
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24. Scheme 21: Synthesis of levofloxacin.
  
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25. Scheme 22: Alternative approach to the levofloxacin core 1.125.
  
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26. Figure 3: Structures of nifedipine, amlodipine and clevidipine.
  
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27. Scheme 23: Mg₃N₂-mediated synthesis of nifedipine.
  
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28. Scheme 24: Synthesis of rac-amlodipine as besylate salt.
  
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29. Scheme 25: Aza Diels–Alder approach towards amlodipine.
  
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30. Scheme 26: Routes towards clevidipine.
  
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31. Figure 4: Examples of piperidine containing drugs.
  
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32. Figure 5: Discovery of tiagabine based on early leads.
  
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33. Scheme 27: Synthetic sequences to tiagabine.
  
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34. Figure 6: Structures of solifenacin (2.57) and muscarine (2.58).
  
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35. Scheme 28: Enantioselective synthesis of solifenacin.
  
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36. Figure 7: Structures of DPP-4 inhibitors of the gliptin-type.
  
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37. Scheme 29: Formation of inactive diketopiperazines from cis-rotameric precursors.
  
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38. Figure 8: Co-crystal structure of carmegliptin bound in the human DPP-4 active site (PDB 3kwf).
  
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39. Scheme 30: Improved route to carmegliptin.
  
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40. Figure 9: Structures of lamivudine and zidovudine.
  
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41. Scheme 31: Typical routes accessing uracil, thymine and cytosine.
  
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42. Scheme 32: Coupling between pyrimidones and riboses via the Vorbrüggen nucleosidation.
  
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43. Scheme 33: Synthesis of lamivudine.
  
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44. Scheme 34: Synthesis of raltegravir.
  
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45. Scheme 35: Mechanistic studies on the formation of 3.22.
  
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46. Figure 10: Structures of selected pyrimidine containing drugs.
  
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47. Scheme 36: General preparation of pyrimidines and dihydropyrimidones.
  
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48. Scheme 37: Synthesis of imatinib.
  
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49. Scheme 38: Flow synthesis of imatinib.
  
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50. Scheme 39: Syntheses of erlotinib.
  
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51. Scheme 40: Synthesis of erlotinib proceeding via Dimroth rearrangement.
  
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52. Scheme 41: Synthesis of lapatinib.
  
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53. Scheme 42: Synthesis of rosuvastatin.
  
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54. Scheme 43: Alternative preparation of the key aldehyde towards rosuvastatin.
  
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55. Figure 11: Structure comparison between nicotinic acetylcholine receptor agonists.
  
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56. Scheme 44: Syntheses of varenicline and its key building block 4.5.
  
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57. Scheme 45: Synthetic access to eszopiclone and brimonidine via quinoxaline intermediates.
  
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58. Figure 12: Bortezomib bound in an active site of the yeast 20S proteasome ([114], pdb 2F16).
  
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59. Scheme 46: Asymmetric synthesis of bortezomib.
  
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60. Figure 13: Structures of some prominent piperazine containing drugs.
  
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61. Figure 14: Structural comparison between the core of aplaviroc (4.35) and a type-1 β-turn (4.36).
  
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62. Scheme 47: Examplary synthesis of an aplaviroc analogue via the Ugi-MCR.
  
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63. Scheme 48: Syntheses of azelastine (5.1).
  
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64. Figure 15: Structures of captopril, enalapril and cilazapril.
  
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65. Scheme 49: Synthesis of cilazapril.
  
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66. Figure 16: Structures of lamotrigine, ceftriaxone and azapropazone.
  
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67. Scheme 50: Synthesis of lamotrigine.
  
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68. Scheme 51: Alternative synthesis of lamotrigine (no yields reported).
  
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69. Figure 17: Structural comparison between imiquimod and the related adenosine nucleoside.
  
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70. Scheme 52: Conventional synthesis of imiquimod (no yields reported).
  
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71. Scheme 53: Synthesis of imiquimod.
  
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72. Scheme 54: Synthesis of imiquimod via tetrazole formation (not all yields reported).
  
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73. Figure 18: Structures of various anti HIV-medications.
  
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74. Scheme 55: Synthesis of abacavir.
  
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75. Figure 19: Structures of diazepam compared to modern replacements.
  
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76. Scheme 56: Synthesis of ocinaplon.
  
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77. Scheme 57: Access to zaleplon and indiplon.
  
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78. Scheme 58: Different routes towards the required N-methylpyrazole 6.65 of sildenafil.
  
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79. Scheme 59: Polymer-supported reagents in the synthesis of key aminopyrazole 6.72.
  
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80. Scheme 60: Early synthetic route to sildenafil.
  
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81. Scheme 61: Convergent preparations of sildenafil.
  
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82. Figure 20: Comparison of the structures of sildenafil, tadalafil and vardenafil.
  
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83. Scheme 62: Short route to imidazotriazinones.
  
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84. Scheme 63: Alternative route towards vardenafils core imidazotriazinone (6.95).
  
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85. Scheme 64: Bayer’s approach to the vardenafil core.
  
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86. Scheme 65: Large scale synthesis of vardenafil.
  
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87. Scheme 66: Mode of action of temozolomide (6.105) as methylating agent.
  
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88. Scheme 67: Different routes to temozolomide.
  
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89. Scheme 68: Safer route towards temozolomide.
  
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90. Figure 21: Some unreported heterocyclic scaffolds in top market drugs.
  
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Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265

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Synthesis of novel 13α-estrone derivatives by Sonogashira coupling as potential 17β-HSD1 inhibitors

Ildikó Bacsa,
Rebeka Jójárt,
János Wölfling,
Gyula Schneider,
Bianka Edina Herman,
Mihály Szécsi and
Erzsébet Mernyák

Full Research Paper
Published 30 Jun 2017

1337 Accesses

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1. Graphical Abstract
2. Scheme 1: Syntheses of 2- or 4-phenethynyl-13α-estrones (8–11) by Sonogashira coupling.
  
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3. Scheme 2: Partial or full hydrogenation of compounds 8c–11c.
  
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Beilstein J. Org. Chem. 2017, 13, 1303–1309, doi:10.3762/bjoc.13.126

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Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins

Alejandro Castán,
Ramón Badorrey,
José A. Gálvez and
María D. Díaz-de-Villegas

Full Research Paper
Published 27 Mar 2017

1202 Accesses

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1. Graphical Abstract
2. Figure 1: Strategy for the preparation of 2-substituted pyrrolidines C.
  
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3. Scheme 1: Synthesis of the new organocatalyst OC1.
  
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4. Scheme 2: Synthesis of new organocatalyst OC2.
  
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5. Scheme 3: Synthesis of new organocatalyst OC3.
  
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6. Scheme 4: Synthesis of new organocatalysts OC4–OC10.
  
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7. Scheme 5: Synthesis of new organocatalyst OC11.
  
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Beilstein J. Org. Chem. 2017, 13, 612–619, doi:10.3762/bjoc.13.59

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Transition-metal-catalyzed synthesis of phenols and aryl thiols

Yajun Liu,
Shasha Liu and
Yan Xiao

Review
Published 23 Mar 2017

1128 Accesses

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1. Graphical Abstract
2. Figure 1: Examples of drugs bearing phenol or aryl thiol as central structural motifs.
  
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3. Scheme 1: Hydroxylation of aryl halides using biphenylphosphine as ligand.
  
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4. Scheme 2: Hydroxylation of aryl halides using tert-butylphosphine as ligand.
  
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5. Scheme 3: Hydroxylation of aryl halides using imidazole typed phosphine ligands.
  
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6. Scheme 4: [Pd(cod)(CH₂SiMe₃)₂] catalyzed hydroxylation of aryl halides.
  
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7. Scheme 5: Pd/PANI catalyzed hydroxylation of hydroxylation of aryl halides.
  
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8. Scheme 6: MCM-41-dzt-Pd catalyzed hydroxylation of aryl halides.
  
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9. Scheme 7: Hydroxylation of aryl halides using dibenzoylmethane as ligand.
  
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10. Scheme 8: Hydroxylation of aryl halides using 2,2’-bipyridine as ligand.
  
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11. Scheme 9: Hydroxylation of aryl bromides using imidazolyl pyridine as ligand.
  
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12. Scheme 10: Hydroxylation of aryl halides using DMEDA as ligand.
  
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13. Scheme 11: Hydroxylation of aryl halides using PAO as ligand.
  
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14. Scheme 12: Hydroxylation of aryl halides using D-glucose as ligand.
  
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15. Scheme 13: Hydroxylation of aryl halides using INDION-770 as ligand.
  
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16. Scheme 14: PEG-400 mediated hydroxylation of aryl halides.
  
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17. Scheme 15: Hydroxylation of aryl halides using glycolic acid as ligand.
  
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18. Scheme 16: Hydroxylation of aryl halides using L-sodium ascorbate as ligand.
  
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19. Scheme 17: Difunctionalized ethanes mediated hydroxylation of aryl iodides.
  
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20. Scheme 18: Hydroxylation of aryl halides using 2-methyl-8-hydroxylquinoline as ligand.
  
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21. Scheme 19: Hydroxylation of aryl halides using 8-hydroxyquinolin-N-oxide as ligand.
  
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22. Scheme 20: Hydroxylation of aryl halides using lithium pipecolinate as ligand.
  
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23. Scheme 21: Hydroxylation of aryl halides using L-lithium prolinate.
  
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24. Scheme 22: Hydroxylation of aryl halides using triethanolamine as ligand.
  
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25. Scheme 23: CuI-nanoparticle-catalyzed hydroxylation of aryl halides.
  
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26. Scheme 24: Cu-g-C₃N₄-catalyzed hydroxylation of aryl bromides.
  
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27. Scheme 25: Cu(OAc)₂-mediated hydroxylation of (2-pyridyl)arenes.
  
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28. Scheme 26: Removable pyridine moiety directed hydroxylation of arenes.
  
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29. Scheme 27: Removable quinoline moiety directed hydroxylation of arenes.
  
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30. Scheme 28: CuCl₂ catalyzed hydroxylation of benzimidazoles and benzoxazoles.
  
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31. Scheme 29: Disulfide-directed C–H hydroxylation.
  
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32. Scheme 30: Pd(OAc)₂-catalyzed hydroxylation of diarylpyridines.
  
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33. Scheme 31: PdCl₂-catalyzed hydroxylation of 2-arylpyridines.
  
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34. Scheme 32: PdCl₂-catalyzed hydroxylation of 2-arylpyridines.
  
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35. Scheme 33: Pd(OAc)₂-catalyzed hydroxylation of 2-arylpyridines.
  
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36. Scheme 34: Pd(CH₃CN)₂Cl₂-catalyzed hydroxylation of 2-arylpyridines.
  
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37. Scheme 35: Pd(OAc)₂-catalyzed hydroxylation of benzothiazolylarenes.
  
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38. Scheme 36: Pd(OAc)₂ catalyzed hydroxylation of benzimidazolylarenes.
  
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39. Scheme 37: Dioxane mediated hydroxylation of 2-heteroarylarenes.
  
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40. Scheme 38: Hydroxylation of oxime methyl ester.
  
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41. Scheme 39: CN-directed meta-hydroxylation.
  
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42. Scheme 40: Pd(OAc)₂-catalyzed hydroxylation of benzoic acids.
  
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43. Scheme 41: Pd(OAc)_2-catalyzed hydroxylation of biaryl or aryl alkyl ketones.
  
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44. Scheme 42: Pd(OAc)₂ and Pd(TFA)₂ catalyzed hydroxylation of aryl ketones.
  
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45. Scheme 43: Pd(OAc)₂ catalyzed hydroxylation of aryl ketones.
  
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46. Scheme 44: Pd(TFA)₂-catalyzed hydroxylation of aryl phosphonates.
  
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47. Scheme 45: Hydroxy group directed hydroxylation.
  
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48. Scheme 46: [Ru(O₂CMes)₂(p-cymene)] catalyzed hydroxylation of benzamides and aryl ketones.
  
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49. Scheme 47: [RuCl₂(p-cymene)]₂-catalyzed hydroxylation of benzamides and carbamates.
  
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50. Scheme 48: [RuCl₂(p-cymene)]₂ catalyzed hydroxylation of benzaldehydes.
  
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51. Scheme 49: [RuCl₂(p-cymene)]₂ catalyzed hydroxylation of ethyl benzoates, benzamides and carbamates.
  
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52. Scheme 50: Different regioselective ortho-hydroxylation.
  
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53. Scheme 51: Ruthenium-complex-catalyzed hydroxylation of flavones.
  
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54. Scheme 52: Vanadium-catalyzed hydroxylation of arenes.
  
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55. Scheme 53: VOSiW-catalyzed hydroxylation of arenes.
  
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56. Scheme 54: Synthesis of aryl thiols using thiourea as thiol source.
  
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57. Scheme 55: Synthesis of aryl thiols using alkyl thiol as thiol source.
  
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58. Scheme 56: Synthesis of 1-thionaphthol using HS-TIPS as thiol source.
  
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59. Scheme 57: Synthesis of aryl thiols using sodium thiosulfate as thiol source.
  
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60. Scheme 58: Synthesis of thiophenol using thiobenzoic acid as thiol source.
  
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61. Scheme 59: Synthesis of aryl thiols using sulfur powder as thiol source.
  
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62. Scheme 60: CuI-nanoparticles catalyzed synthesis of aryl thiols.
  
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63. Scheme 61: Synthesis of aryl thiols using Na₂S·5H₂O as thiol source.
  
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64. Scheme 62: Synthesis of aryl thiols using 1,2-ethanedithiol as thiol source.
  
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Beilstein J. Org. Chem. 2017, 13, 589–611, doi:10.3762/bjoc.13.58

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A concise flow synthesis of indole-3-carboxylic ester and its derivatisation to an auxin mimic

Marcus Baumann,
Ian R. Baxendale and
Fabien Deplante

Full Research Paper
Published 29 Nov 2017

1049 Accesses

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1. Graphical Abstract
2. Figure 1: Natural indole containing molecules 1–7 of biological importance and synthetic auxin analogue 8 req...
  
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3. Scheme 1: Synthetic strategy towards desired indole product 8.
  
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4. Scheme 2: Initial flow reactor setup for the synthesis of intermediate 11.
  
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5. Scheme 3: Coflore ACR setup for the synthesis of intermediate 11.
  
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6. Scheme 4: Quenching and work-up of the reaction stream from the Coflore ACR for the synthesis intermediate 11....
  
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7. Figure 2: X-ray structure of intermediate 11, and reductive cyclisation products 12 and 14, assigned structur...
  
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8. Scheme 5: Stepwise reduction of intermediate 11 under hydrogenation conditions. * Indicates potential tautome...
  
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9. Scheme 6: Flow sequence for the construction of product 8.
  
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10. Scheme 7: Assembled process for flow synthesis of product 8 with yields and throughputs.
  
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Beilstein J. Org. Chem. 2017, 13, 2549–2560, doi:10.3762/bjoc.13.251

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Six-fold C–H borylation of hexa-peri-hexabenzocoronene

Mai Nagase,
Kenta Kato,
Akiko Yagi,
Yasutomo Segawa and
Kenichiro Itami

Full Research Paper
Published 13 Mar 2020

1004 Accesses

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1. Graphical Abstract
2. Figure 1: C–H functionalization of HBCs. (a) Perchlorinated HBC. (b) Borylated HBC substituted by 2,4,6-trime...
  
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3. Figure 2: Synthesis of hexaborylated HBC 1. (a) Solvent screening of six-fold C–H borylation of unsubstituted...
  
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4. Figure 3: The structure of 1 confirmed by X-ray crystallographic analysis. (a) ORTEP drawing of 1 with therma...
  
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5. Figure 4: Photophysical properties of 1. (a) UV–vis absorption (solid lines) spectra, fluorescence (dotted li...
  
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Beilstein J. Org. Chem. 2020, 16, 391–397, doi:10.3762/bjoc.16.37

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