Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

Sambasivarao Kotha,
Milind Meshram and
Chandravathi Chakkapalli

Review
Published 21 Sep 2018

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1. Graphical Abstract
2. Figure 1: Various catalysts used for metathesis reactions.
  
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3. Scheme 1: SM coupling and RCM protocol to substituted indene derivative 10.
  
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4. Scheme 2: Synthesis of polycycles via SM and RCM approach.
  
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5. Figure 2: Various angucyclines.
  
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6. Scheme 3: SM coupling and RCM protocol to the benz[a]anthracene skeleton 26.
  
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7. Scheme 4: Synthesis of substituted spirocycles via RCM and SM sequence.
  
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8. Scheme 5: Synthesis of highly functionalized bis-spirocyclic derivative 37.
  
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9. Scheme 6: Synthesis of spirofluorene derivatives via RCM and SM coupling sequence.
  
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10. Scheme 7: Synthesis of truxene derivatives via RCM and SM coupling.
  
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11. Scheme 8: Synthesis of substituted isoquinoline derivative via SM and RCM protocol.
  
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12. Scheme 9: Synthesis to 8-aryl substituted coumarin 64 via RCM and SM sequence.
  
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13. Scheme 10: Synthesis of cyclic sulfoximine 70 via SM and RCM as key steps.
  
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14. Scheme 11: Synthesis of 1-benzazepine derivative 75 via SM and RCM as key steps.
  
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15. Scheme 12: Synthesis of naphthoxepine derivative 79 via RCM followed by SM coupling.
  
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16. Scheme 13: Sequential CM and SM coupling approach to Z-stilbene derivative 85.
  
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17. Scheme 14: Synthesis of substituted trans-stilbene derivatives via SM coupling and RCM.
  
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18. Scheme 15: Synthesis of biaryl derivatives via sequential EM, DA followed by SM coupling.
  
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19. Scheme 16: Synthesis of the dibenzocyclooctadiene core of schisandrene.
  
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20. Scheme 17: Synthesis of cyclophane 115 via SM coupling and RCM as key steps.
  
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21. Scheme 18: Synthesis of cyclophane 120 and 122 via SM coupling and RCM as key steps.
  
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22. Scheme 19: Synthesis of cyclophanes via SM and RCM.
  
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23. Scheme 20: Synthesis of MK-6325 (141) via RCM and SM coupling.
  
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Beilstein J. Org. Chem. 2018, 14, 2468–2481, doi:10.3762/bjoc.14.223

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Synthesis of eunicellane-type bicycles embedding a 1,3-cyclohexadiene moiety

Alex Frichert,
Peter G. Jones and
Thomas Lindel

Full Research Paper
Published 20 Sep 2018

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1. Graphical Abstract
2. Figure 1: Bicyclic eunicellane-type diterpenes.
  
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3. Figure 2: Synthetic eunicellane-type compounds with benzene partial structure.
  
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4. Scheme 1: Access to ketoester 14 that did not cyclize to the ethyl vinyl ether under McMurry conditions.
  
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5. Scheme 2: Synthesis of the 1,3-cyclohexadiene-containing eunicellane-type [8.4.0]bicycle 18 by McMurry coupli...
  
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6. Figure 3: Preferred conformations of diastereomeric diols 18 and 19 including decisive NOESY correlations.
  
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7. Scheme 3: Assembly of the envisaged cyclization precursor 27.
  
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8. Scheme 4: Structure analysis of diastereomeric cyanohydrins 29 and 30.
  
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9. Scheme 5: Formation of allenes 32 and 34 from sterically crowded propargylic alcohol 31.
  
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Beilstein J. Org. Chem. 2018, 14, 2461–2467, doi:10.3762/bjoc.14.222

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Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source

Tetsuaki Fujihara and
Yasushi Tsuji

Review
Published 19 Sep 2018

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1. Graphical Abstract
2. Scheme 1: Optimization of the Co-catalyzed carboxylation of 1a.
  
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3. Scheme 2: Co-catalyzed carboxylation of propargyl acetates 1.
  
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4. Scheme 3: Plausible reaction mechanism for the Co-catalyzed carboxylation of propargyl acetates 1.
  
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5. Scheme 4: Optimization of the Co-catalyzed carboxylation of 3a.
  
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6. Scheme 5: Co-catalyzed carboxylation of vinyl triflates 3.
  
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7. Scheme 6: Co-catalyzed carboxylation of a sterically hindered aryl triflate 5.
  
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8. Scheme 7: Optimization of the Co-catalyzed carboxylation of 7a.
  
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9. Scheme 8: Scope of the reductive carboxylation of α,β-unsaturated nitriles 7.
  
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10. Scheme 9: Scope of the carboxylation of α,β-unsaturated carboxamides 9.
  
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11. Scheme 10: Optimization of the Co-catalyzed carboxylation of 11a.
  
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12. Scheme 11: Scope of the carboxylation of allylarenes 11.
  
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13. Scheme 12: Scope of the carboxylation of 1,4-diene derivatives 14.
  
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14. Scheme 13: Plausible reaction mechanism for the Co-catalyzed C(sp³)–H carboxylation of allylarenes.
  
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15. Scheme 14: Optimization of the Co-catalyzed carboxyzincation of 16a.
  
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16. Scheme 15: Derivatization of the carboxyzincated product.
  
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17. Scheme 16: Co-catalyzed carboxyzincation of alkynes 16.
  
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18. Scheme 17: Plausible reaction mechanism for the Co-catalyzed carboxyzincation of alkynes 16.
  
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19. Scheme 18: Co-catalyzed four-component coupling of alkynes 16, acrylates 18, CO₂, and zinc.
  
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20. Scheme 19: Proposed reaction mechanism for the Co-catalyzed four-component coupling.
  
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21. Scheme 20: Visible-light-driven hydrocarboxylation of alkynes.
  
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22. Scheme 21: Visible-light-driven synthesis of γ-hydroxybutenolides from ortho-ester-substituted aryl alkynes.
  
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23. Scheme 22: One-pot synthesis of coumarines and 2-quinolones via hydrocarboxylation/alkyne isomerization/cycliz...
  
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24. Scheme 23: Proposed reaction mechanism for the Co-catalyzed carboxylative cyclization of ortho-substituted aro...
  
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25. Scheme 24: Rh-catalyzed carboxylation of arylboronic esters 25.
  
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26. Scheme 25: Rh-catalyzed carboxylation of alkenylboronic esters 27.
  
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27. Scheme 26: Plausible reaction mechanism for the Rh-catalyzed carboxylation of arylboronic esters 25.
  
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28. Scheme 27: Ligand effect on the Rh-catalyzed carboxylation of 2-phenylpyridine 29a.
  
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29. Scheme 28: Rh-catalyzed chelation-assisted C(sp²)–H bond carboxylation with CO₂.
  
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30. Scheme 29: Reaction mechanism for the Rh-catalyzed C(sp²)–H carboxylation of 2-pyridylarenes 29.
  
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31. Scheme 30: Carboxylation of C(sp²)–H bond with CO₂.
  
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32. Scheme 31: Carboxylation of C(sp²)–H bond with CO₂.
  
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33. Scheme 32: Reaction mechanism for the Rh-catalyzed C(sp²)–H carboxylation of 2-arylphenols 34.
  
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34. Scheme 33: Hydrocarboxylation of styrene derivatives with CO₂.
  
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35. Scheme 34: Hydrocarboxylation of α,β-unsaturated esters with CO₂.
  
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36. Scheme 35: Asymmetric hydrocarboxylation of α,β-unsaturated esters with CO₂.
  
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37. Scheme 36: Proposed reaction mechanism for the Rh-catalyzed hydrocarboxylation of C–C double bonds with CO₂.
  
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38. Scheme 37: Visible-light-driven hydrocarboxylation with CO₂.
  
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39. Scheme 38: Visible-light-driven Rh-catalyzed hydrocarboxylation of C–C double bonds with CO₂.
  
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40. Scheme 39: Optimization of reaction conditions on the Rh-catalyzed [2 + 2 + 2] cycloaddition of diyne 42a and ...
  
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41. Scheme 40: [2 + 2 + 2] Cycloaddition of diyne and CO₂.
  
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42. Scheme 41: Proposed reaction pathways for the Rh-catalyzed [2 + 2 + 2] cycloaddition of diyne and CO₂.
  
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Beilstein J. Org. Chem. 2018, 14, 2435–2460, doi:10.3762/bjoc.14.221

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Efficient catalytic alkyne metathesis with a fluoroalkoxy-supported ditungsten(III) complex

Henrike Ehrhorn,
Janin Schlösser,
Dirk Bockfeld and
Matthias Tamm

Full Research Paper
Published 18 Sep 2018

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1. Graphical Abstract
2. Figure 1: Selected homogeneous catalysts for alkyne metathesis.
  
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3. Scheme 1: Synthesis of alkylidyne complex V from bimetallic [(t-BuO)₃W≡W(Ot-Bu)₃]; the catalytically active d...
  
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4. Scheme 2: Synthesis of hexakis(fluoroalkoxide) dimers Mo2F6 [73] and W2F3.
  
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5. Figure 2: Molecular structure of W2F3·NHMe₂ with thermal displacement parameters drawn at 50% probability. Hy...
  
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6. Scheme 3: Preparation of the alkylidyne complex W^PhF3.
  
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7. Figure 3: Molecular structure of W^PhF3 with thermal displacement parameters drawn at 50% probability. Hydroge...
  
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8. Scheme 4: Self-metathesis of 1-phenyl-1-propyne derivatives by tungsten complexes W2F3 and W^PhF3.
  
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9. Figure 4: Conversion versus time diagram for the self-metathesis of 1-phenyl-1-propyne catalyzed by 0.5 mol % ...
  
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Beilstein J. Org. Chem. 2018, 14, 2425–2434, doi:10.3762/bjoc.14.220

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Microfluidic light-driven synthesis of tetracyclic molecular architectures

Javier Mateos,
Nicholas Meneghini,
Marcella Bonchio,
Nadia Marino,
Tommaso Carofiglio,
Xavier Companyó and
Luca Dell’Amico

Letter
Published 17 Sep 2018

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1. Graphical Abstract
2. Figure 1: a) Light-driven reaction between 2-MBP A and maleimide B for the synthesis of C through a [4 + 2] c...
  
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3. Figure 2: Generality and limits of the light-driven [4 + 2] cyclization reaction between 2-MBP 1a–g and couma...
  
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4. Figure 3: Generality and limits of the light-driven [4 + 2] cyclization reaction between 2-MBP 1a–f and chrom...
  
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5. Scheme 1: MFP parallel setup for higher scale production of 4a (top) and different molecular scaffolds 6a–9a ...
  
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Beilstein J. Org. Chem. 2018, 14, 2418–2424, doi:10.3762/bjoc.14.219

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Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal

Antonio Arcadi,
Sandro Cacchi,
Giancarlo Fabrizi,
Francesca Ghirga,
Antonella Goggiamani,
Antonia Iazzetti and
Fabio Marinelli

Full Research Paper
Published 14 Sep 2018

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1. Graphical Abstract
2. Scheme 1: Synthesis of 6-trifluoromethyl-12-aryl(vinyl)indolo[1,2-c]quinazolines 4.
  
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3. Scheme 2: Present and previously reported reactions starting from 5. DMFDMA: dimethylformamide dimethyl aceta...
  
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4. Scheme 3: Two-step synthesis of 12-arylindolo[1,2-c]quinazoline 10a.
  
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5. Scheme 4: Synthesis of indoles 14.
  
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6. Scheme 5: Sequential preparation of 13a from 15a.
  
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Beilstein J. Org. Chem. 2018, 14, 2411–2417, doi:10.3762/bjoc.14.218

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Nucleoside macrocycles formed by intramolecular click reaction: efficient cyclization of pyrimidine nucleosides decorated with 5'-azido residues and 5-octadiynyl side chains

Jiang Liu,
Peter Leonard,
Sebastian L. Müller,
Constantin Daniliuc and
Frank Seela

Letter
Published 13 Sep 2018

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1. Graphical Abstract
2. Figure 1: Energy-minimized models of the two macrocycles derived from dC (left) and dU (right) acquired by MM+...
  
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3. Scheme 1: Synthesis of the 5’-azido-2’,5’-dideoxyribonucleoside 2, the macrocycle 4 and the dimeric compounds ...
  
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4. Scheme 2: Synthesis of 5’-azido-2’,5’-dideoxyribonucleoside 7 and nucleoside macrocycle 8.
  
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5. Figure 2: A perspective view of 8 showing the atomic numbering scheme. Displacement ellipsoids are drawn at t...
  
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6. Figure 3: The crystal packing of 8 shows the intramolecular hydrogen-bonding network (projection parallel to ...
  
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7. Figure 4: N- and S-conformation for cyclonucleoside 8. B corresponds to nucleobase. ax: axial; eq: equatorial....
  
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Beilstein J. Org. Chem. 2018, 14, 2404–2410, doi:10.3762/bjoc.14.217

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The mechanochemical synthesis of quinazolin-4(3H)-ones by controlling the reactivity of IBX

Md Toufique Alam,
Saikat Maiti and
Prasenjit Mal

Full Research Paper
Published 12 Sep 2018

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1. Graphical Abstract
2. Figure 1: a) Explosion was observed when an arylamine was mixed with aldehydes in the presence of IBX. b) Ben...
  
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3. Figure 2: Comparison of the current work with the existing literature reports.
  
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4. Figure 3: Synthesis of quinazolin-4(3H)-one derivatives from the reaction of 1 with liquid aldehydes. ^aYields...
  
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5. Figure 4: Synthesis of quinazolin-4(3H)-one derivatives from reaction of 1 and solid aldehydes. ^aYields with ...
  
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6. Figure 5: Crystal structure of 3a (CCDC No. 1823611).
  
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7. Figure 6: Plausible mechanism for the quinazolin-4(3H)-ones synthesis using IBX.
  
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8. Scheme 1: Large scale synthesis of 3a.
  
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Beilstein J. Org. Chem. 2018, 14, 2396–2403, doi:10.3762/bjoc.14.216

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Correction: Varioloid A, a new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291

Peng Zhang,
Xiao-Ming Li,
Xin-Xin Mao,
Attila Mándi,
Tibor Kurtán and
Bin-Gui Wang

Correction
Published 12 Sep 2018

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1. Figure 1: Varioloids A–D.
  
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Original
Article

Beilstein J. Org. Chem. 2018, 14, 2394–2395, doi:10.3762/bjoc.14.215

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Some mechanistic aspects regarding the Suzuki–Miyaura reaction between selected ortho-substituted phenylboronic acids and 3,4,5-tribromo-2,6-dimethylpyridine

Piotr Pomarański,
Piotr Roszkowski,
Jan K. Maurin,
Armand Budzianowski and
Zbigniew Czarnocki

Full Research Paper
Published 11 Sep 2018

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1. Graphical Abstract
2. Figure 1: Structures of stereoisomers of 3,4,5-tris(2-methoxyphenyl)-2,6-dimethylpyridines determined by X-ra...
  
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3. Figure 2: Graphical representation of kinetic, time-dependent ¹H NMR analysis of (syn)-7 (100 °C).
  
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4. Figure 3: Graphical representation of kinetic, time-dependent ¹H NMR analysis of (syn)-10 (120 °C).
  
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5. Figure 4: HT-NMR (300 MHz, DMSO-d₆) spectra of A) (syn)-7. B) (syn)-10. Only the upfield (ca. 3.4–4 ppm) regi...
  
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6. Figure 5: Summary of the results for coupling with ortho-substituted phenylboronic acid for triaryl products.
  
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7. Figure 6: Summary of results for coupling with ortho-substituted phenylboronic acid for diaryl products.
  
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8. Figure 7: Proposed intermediates for the 1,2-addition of 5 with methoxy group. A) Oxidative addition step. B)...
  
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9. Figure 8: Proposed intermediates for the 1,3-addition with methoxy group. A) Oxidative addition step. B) Tran...
  
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10. Figure 9: Proposed intermediates for the 1,2-addition with chlorine atom. A) Oxidative addition step. B) Tran...
  
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11. Figure 10: Proposed intermediates for the 1,3-addition with chlorine atom. A) Oxidative addition step. B) Tran...
  
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Beilstein J. Org. Chem. 2018, 14, 2384–2393, doi:10.3762/bjoc.14.214

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Practical tetrafluoroethylene fragment installation through a coupling reaction of (1,1,2,2-tetrafluorobut-3-en-1-yl)zinc bromide with various electrophiles

Ken Tamamoto,
Shigeyuki Yamada and
Tsutomu Konno

Full Research Paper
Published 11 Sep 2018

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1. Graphical Abstract
2. Figure 1: Functional molecules with CF₂CF₂-fragment.
  
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3. Scheme 1: Preparation and synthetic applications of 2-Zn.
  
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4. Figure 2: Recovery yield of 2-Zn in DMF (ca. 0.70 M) after stirring at various temperature conditions.
  
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5. Figure 3: Copper(I)-catalyzed cross-coupling reaction of 2-Zn with various iodoarene derivatives. NMR (isolat...
  
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6. Scheme 2: Multigram-scale cross-coupling of 2-Zn with iodoarenes.
  
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7. Scheme 3: Synthesis of a CF₂CF₂ group containing tolane derivative.
  
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8. Figure 4: Copper(I)-catalyzed cross-coupling reaction of 2-Zn with various acid chlorides. NMR yields (isolat...
  
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Beilstein J. Org. Chem. 2018, 14, 2375–2383, doi:10.3762/bjoc.14.213

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A challenging redox neutral Cp*Co(III)-catalysed alkylation of acetanilides with 3-buten-2-one: synthesis and key insights into the mechanism through DFT calculations

Andrew Kenny,
Alba Pisarello,
Arron Bird,
Paula G. Chirila,
Alex Hamilton and
Christopher J. Whiteoak

Full Research Paper
Published 10 Sep 2018

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1. Graphical Abstract
2. Scheme 1: (a) Our previously reported Cp*Co(III) redox-neutral coupling of 3-buten-2-one to benzamides, (b) p...
  
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3. Scheme 2: Summary of reaction conditions optimisation.
  
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4. Scheme 3: Substrate scope of Cp*Co(III)-catalysed coupling of 3-buten-2-one with functionalised acetanilides....
  
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5. Figure 1: Mechanistic pathway for Cp*Co(III)-catalysed alkylation of acetanilide with 3-buten-2-one obtained ...
  
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6. Figure 2: Comparison between energies during the Cp*Co(III)-catalysed coupling of 3-buten-2-one with acetanil...
  
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7. Figure 3: Comparative visualisation of bcp for Int 2_ketone with the acetanilide (left) and benzamide substrat...
  
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8. Scheme 4: Competitive experiment between coupling to acetanilide (ring A) or benzamide (ring B). ^aMajor produ...
  
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Beilstein J. Org. Chem. 2018, 14, 2366–2374, doi:10.3762/bjoc.14.212

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Non-metal-templated approaches to bis(borane) derivatives of macrocyclic dibridgehead diphosphines via alkene metathesis

Tobias Fiedler,
Michał Barbasiewicz,
Michael Stollenz and
John A. Gladysz

Full Research Paper
Published 07 Sep 2018

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1. Graphical Abstract
2. Scheme 1: Syntheses of gyroscope like platinum and rhodium complexes and dibridgehead diphosphines derived th...
  
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3. Scheme 2: Synthesis and alkene metathesis of the monophosphorus precursor 1·BH₃.
  
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4. Figure 1: The ¹³C{¹H} NMR spectra (CDCl₃, 100 MHz) of in,out-2·2BH₃, (in,in/out,out)-2·2BH₃, 6·2BH₃, and the ...
  
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5. Scheme 3: Synthesis of the diphosphorus precursor 11·2BH₃.
  
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6. Scheme 4: Truncated approaches to the diphosphorus precursor 11·2BH₃ from 10.
  
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7. Scheme 5: Alkene metathesis of the diphosphorus precursor 11·2BH₃.
  
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8. Scheme 6: Schematic comparison of the key alkene metathesis steps in Scheme 2 and Scheme 5.
  
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9. Scheme 7: Steps that set the in,in/out,out vs in,out stereochemistry of 2·2BH₃ in Scheme 2 and Scheme 5.
  
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10. Scheme 8: Another non-metal-templated approach to dibridgehead diphosphorus compounds.
  
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11. Scheme 9: Previously synthesized dibridgehead diphosphine diboranes.
  
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12. Scheme 10: Alkene metathesis of the tetraalkenyldiphosphine diborane 19·2BH₃.
  
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Beilstein J. Org. Chem. 2018, 14, 2354–2365, doi:10.3762/bjoc.14.211

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Catalyst-free synthesis of 4-acyl-NH-1,2,3-triazoles by water-mediated cycloaddition reactions of enaminones and tosyl azide

Lu Yang,
Yuwei Wu,
Yiming Yang,
Chengping Wen and
Jie-Ping Wan

Full Research Paper
Published 07 Sep 2018

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1. Graphical Abstract
2. Figure 1: Scope of the water-mediated synthesis of 4-acyl-NH-1,2,3-triazoles. General conditions: enaminone 1...
  
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3. Scheme 1: The gram scale synthesis of 3a: (a) before reaction; (b) completed reaction; (c) the purified produ...
  
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4. Scheme 2: The proposed reaction mechanism.
  
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Beilstein J. Org. Chem. 2018, 14, 2348–2353, doi:10.3762/bjoc.14.210

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A novel and practical asymmetric synthesis of eptazocine hydrobromide

Ruipeng Li,
Zhenren Liu,
Liang Chen,
Jing Pan,
Kuaile Lin and
Weicheng Zhou

Full Research Paper
Published 06 Sep 2018

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1. Graphical Abstract
2. Scheme 1: Commercial process for the synthesis of 1.
  
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3. Scheme 2: Previous work about asymmetric synthesis of I-13a.
  
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4. Scheme 3: Asymmetric synthesis of 1.
  
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5. Scheme 4: The second strategy for the asymmetric synthesis of 1.
  
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Beilstein J. Org. Chem. 2018, 14, 2340–2347, doi:10.3762/bjoc.14.209

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Bioinspired cobalt cubanes with tunable redox potentials for photocatalytic water oxidation and CO₂ reduction

Zhishan Luo,
Yidong Hou,
Jinshui Zhang,
Sibo Wang and
Xinchen Wang

Full Research Paper
Published 05 Sep 2018

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1. Graphical Abstract
2. Figure 1: (a) Molecular structures of the Co₄O₄ cubane catalysts. (b) Ball-and-stick representation of comple...
  
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3. Figure 2: UV–vis absorption spectra of 1-R in H₂O based on measurements in 10⁻⁴ M solution. Inset: scale from...
  
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4. Figure 3: Correlation of Hammett constants σ_p for the different ligands with midpoint potentials (E_1/2) in co...
  
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5. Figure 4: Linear sweep voltammetry of 1-R (0.3 mM) or Co(NO₃)₂·6H₂O (1.2 mM); (a) at a 100 mV/s scan rate in ...
  
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6. Figure 5: The activity of 1-R for (a) water oxidation and (b) CO₂ reduction. (c) Long-time course of water ox...
  
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7. Figure 6: Long-time course of water oxidation for 1-CN and Co²⁺ under UV–vis light irradiation (λ >300 nm).
  
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Beilstein J. Org. Chem. 2018, 14, 2331–2339, doi:10.3762/bjoc.14.208

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Semi-synthesis and insecticidal activity of spinetoram J and its D-forosamine replacement analogues

Kai Zhang,
Jiarong Li,
Honglin Liu,
Haiyou Wang and
Lamusi A

Full Research Paper
Published 04 Sep 2018

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1. Graphical Abstract
2. Figure 1: Structures of spinosad and spinetoram.
  
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3. Scheme 1: Comparison of previous synthesis and self-protection synthesis.
  
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4. Scheme 2: Synthesis of spinetoram J from spinosyn A based on a self-protection strategy.
  
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5. Scheme 3: Synthesis of spinetoram J analogues.
  
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Beilstein J. Org. Chem. 2018, 14, 2321–2330, doi:10.3762/bjoc.14.207

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Stereoselective total synthesis and structural revision of the diacetylenic diol natural products strongylodiols H and I

Pamarthi Gangadhar,
Sayini Ramakrishna,
Ponneri Venkateswarlu and
Pabbaraja Srihari

Full Research Paper
Published 04 Sep 2018

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1. Graphical Abstract
2. Figure 1: Proposed structures of a selection of diacetylenic polyol natural products.
  
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3. Scheme 1: Retrosynthesis of strongylodiols H and I.
  
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4. Scheme 2: Synthesis of alkyne 19 and iodo intermediate 21. Reagents and conditions: (a) n-BuLi, THF, −78 °C t...
  
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5. Scheme 3: Stereoselective synthesis of (R)-25. Reagents and conditions: (a) CuCl, NH₂OH·HCl, 30% n-BuNH₂, Et₂...
  
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6. Figure 2: Absolute configuration analysis of alcohol 25. ∆δ = δ_S − δ_R for the (R)- and (S)-MTPA ester of alco...
  
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7. Scheme 4: Synthesis of strongylodiol H (9). Reagents and conditions: (a) TBDPSCl, imidazole, CH₂Cl₂, 0 °C to ...
  
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8. Figure 3: Previously proposed and revised structure of strongylodiol H (9).
  
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9. Scheme 5: Synthesis of compound 25a. Reagents and conditions: (a) (R)-CBS catalyst, BH₃·DMS, −50 °C, 16 h, 86...
  
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10. Scheme 6: Synthesis of strongylodiol I (10a). Reagents and conditions: (a) (i) TBDPSCl, imidazole, CH₂Cl₂, 0 ...
  
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Beilstein J. Org. Chem. 2018, 14, 2313–2320, doi:10.3762/bjoc.14.206

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One-pot synthesis of epoxides from benzyl alcohols and aldehydes

Edwin Alfonzo,
Jesse W. L. Mendoza and
Aaron B. Beeler

Full Research Paper
Published 03 Sep 2018

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1. Graphical Abstract
2. Scheme 1: One-pot synthesis of epoxides from benzyl alcohols and aldehydes.
  
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3. Figure 1: Scope of the one-pot synthesis of epoxides from benzyl alcohols and aldehydes.
  
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4. Scheme 2: mCPBA epoxidation of electron-rich stilbene derivatives.
  
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5. Figure 2: Scope of the reaction with electron-rich alcohols and aldehydes.
  
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Beilstein J. Org. Chem. 2018, 14, 2308–2312, doi:10.3762/bjoc.14.205

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The enzymes of microbial nicotine metabolism

Paul F. Fitzpatrick

Review
Published 31 Aug 2018

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Album
1. Graphical Abstract
2. Scheme 1: Nicotine catabolism in A. nicotinovorans. The respective gene names are given in parentheses.
  
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3. Scheme 2: Hydroxylation of nicotine by the molybdopterin cofactor of nicotine dehydrogenase.
  
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4. Figure 1: Overlay of the structure of LHNO (blue, pdb file 3NG7) with that of human MAO B (orange, pdb file 2...
  
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5. Scheme 3: Proposed mechanism of LHNO [21].
  
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6. Scheme 4: Mechanism of LHNO.
  
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7. Figure 2: Overlay of the structures of DHNO (blue, pdb file 2bvf) and tirandamycin oxidase (orange, pdb file ...
  
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8. Scheme 5: Proposed mechanism for DHNO [27].
  
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9. Scheme 6: Mechanism of 2,6-dihydroxypseudooxynicotine hydrolase [37].
  
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10. Figure 3: Overlay of structures of salicylate hydroxylase (orange, pdb file 5evy) and 2,3-dihydroxypyridine 3...
  
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11. Scheme 7: Mechanism of 2,3-dihydroxypyridine 3-hydroxylase [42].
  
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12. Scheme 8: The pyrrolidine pathway for nicotine degradation by pseudomonads. The gene names for P. putida S16 ...
  
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13. Figure 4: Overlay of the structure of LHNO (magenta, pdb file 3NG7) with that of NicA2 (magenta, pdb file 5tt...
  
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14. Scheme 9: The pseudooxynicotine amine oxidase reaction.
  
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15. Scheme 10: Mechanism of HspB [59].
  
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16. Scheme 11: Hybrid pyridine/pyrrolidine pathway for nicotine metabolism in Agrobacter tumefaciens S33 (black), ...
  
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Beilstein J. Org. Chem. 2018, 14, 2295–2307, doi:10.3762/bjoc.14.204

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Determining the predominant tautomeric structure of iodine-based group-transfer reagents by ¹⁷O NMR spectroscopy

Nico Santschi,
Cody Ross Pitts,
Benson J. Jelier and
René Verel

Full Research Paper
Published 30 Aug 2018

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1. Graphical Abstract
2. Figure 1: Tautomerism in iodine-based group-transfer reagents probed by ¹⁷O NMR spectroscopy (A) and key stru...
  
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3. Figure 2: Assignment of acyclic (b) and cyclic (a) structures to 5 and 6, respectively, based on computed iso...
  
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4. Figure 3: Protonation of 4a with trifluoroacetic acid (5 equiv) affords 4c, followed by ¹⁷O NMR spectroscopy.
  
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Beilstein J. Org. Chem. 2018, 14, 2289–2294, doi:10.3762/bjoc.14.203

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Hydroarylations by cobalt-catalyzed C–H activation

Rajagopal Santhoshkumar and
Chien-Hong Cheng

Review
Published 29 Aug 2018

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Album
1. Graphical Abstract
2. Scheme 1: Cobalt-catalyzed C–H carbonylation.
  
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3. Scheme 2: Hydroarylation by C–H activation.
  
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4. Scheme 3: Pathways for cobalt-catalyzed hydroarylations.
  
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5. Scheme 4: Co-catalyzed hydroarylation of alkynes with azobenzenes.
  
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6. Scheme 5: Co-catalyzed hydroarylation of alkynes with 2-arylpyridines.
  
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7. Scheme 6: Co-catalyzed addition of azoles to alkynes.
  
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8. Scheme 7: Co-catalyzed addition of indoles to alkynes.
  
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9. Scheme 8: Co-catalyzed hydroarylation of alkynes with imines.
  
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10. Scheme 9: A plausible pathway for Co-catalyzed hydroarylation of alkynes.
  
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11. Scheme 10: Co-catalyzed anti-selective C–H addition to alkynes.
  
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12. Scheme 11: Co(III)-catalyzed hydroarylation of alkynes with indoles.
  
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13. Scheme 12: Co(III)-catalyzed branch-selective hydroarylation of alkynes.
  
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14. Scheme 13: Co(III)-catalyzed hydroarylation of terminal alkynes with arenes.
  
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15. Scheme 14: Co(III)-catalyzed hydroarylation of alkynes with amides.
  
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16. Scheme 15: Co(III)-catalyzed C–H alkenylation of arenes.
  
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17. Scheme 16: Co-catalyzed alkylation of substituted benzamides with alkenes.
  
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18. Scheme 17: Co-catalyzed switchable hydroarylation of styrenes with 2-aryl pyridines.
  
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19. Scheme 18: Co-catalyzed linear-selective hydroarylation of alkenes with imines.
  
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20. Scheme 19: Co-catalyzed linearly-selective hydroarylation of alkenes with N–H imines.
  
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21. Scheme 20: Co-catalyzed branched-selective hydroarylation of alkenes with imines.
  
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22. Scheme 21: Mechanism of Co-catalyzed hydroarylation of alkenes.
  
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23. Scheme 22: Co-catalyzed intramolecular hydroarylation of indoles.
  
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24. Scheme 23: Co-catalyzed asymmetric hydroarylation of alkenes with indoles.
  
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25. Scheme 24: Co-catalyzed hydroarylation of alkenes with heteroarenes.
  
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26. Scheme 25: Co(III)-catalyzed hydroarylation of activated alkenes with 2-phenyl pyridines.
  
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27. Scheme 26: Co(III)-catalyzed C–H alkylation of arenes.
  
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28. Scheme 27: Co(III)-catalyzed C2-alkylation of indoles.
  
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29. Scheme 28: Co(III)-catalyzed switchable hydroarylation of alkyl alkenes with indoles.
  
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30. Scheme 29: Co(III)-catalyzed C2-allylation of indoles.
  
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31. Scheme 30: Co(III)-catalyzed ortho C–H alkylation of arenes with maleimides.
  
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32. Scheme 31: Co(III)-catalyzed hydroarylation of maleimides with arenes.
  
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33. Scheme 32: Co(III)-catalyzed hydroarylation of allenes with arenes.
  
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34. Scheme 33: Co-catalyzed hydroarylative cyclization of enynes with carbonyl compounds.
  
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35. Scheme 34: Mechanism for the Co-catalyzed hydroarylative cyclization of enynes with carbonyl compounds.
  
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36. Scheme 35: Co-catalyzed addition of 2-arylpyridines to aromatic aldimines.
  
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37. Scheme 36: Co-catalyzed addition of 2-arylpyridines to aziridines.
  
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38. Scheme 37: Co(III)-catalyzed hydroarylation of imines with arenes.
  
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39. Scheme 38: Co(III)-catalyzed addition of arenes to ketenimines.
  
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40. Scheme 39: Co(III)-catalyzed three-component coupling.
  
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41. Scheme 40: Co(III)-catalyzed hydroarylation of aldehydes.
  
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42. Scheme 41: Co(III)-catalyzed addition of arenes to isocyanates.
  
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Beilstein J. Org. Chem. 2018, 14, 2266–2288, doi:10.3762/bjoc.14.202

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Cobalt bis(acetylacetonate)–tert-butyl hydroperoxide–triethylsilane: a general reagent combination for the Markovnikov-selective hydrofunctionalization of alkenes by hydrogen atom transfer

Xiaoshen Ma and
Seth B. Herzon

Full Research Paper
Published 28 Aug 2018

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Album
1. Graphical Abstract
2. Scheme 1: General mechanism of alkene hydrofunctionalization via HAT.
  
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3. Scheme 2: Reduction of the alkenyl chloride 1 by HAT.
  
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4. Scheme 3: Substrate scope of alkyl-aryl azo compound synthesis via HAT. Conditions: alkene (0.250 mmol), diaz...
  
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Beilstein J. Org. Chem. 2018, 14, 2259–2265, doi:10.3762/bjoc.14.201

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Novel photochemical reactions of carbocyclic diazodiketones without elimination of nitrogen – a suitable way to N-hydrazonation of C–H-bonds

Liudmila L. Rodina,
Xenia V. Azarova,
Jury J. Medvedev,
Dmitrij V. Semenok and
Valerij A. Nikolaev

Full Research Paper
Published 28 Aug 2018

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1. Graphical Abstract
2. Figure 1: The structures of carbocyclic diazodiketones 1a–g and C–H-donating tetrahydrofuran used in the proj...
  
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3. Figure 2: Molecular structure of hydrazone 2b as determined by X-ray analysis data (Olex2 plot with 50% proba...
  
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4. Scheme 1: Photochemical cycloelimination of furans from hydrazones 2d,e.
  
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5. Scheme 2: Different pathways of diazodiketones 1 light-induced reactions in the singlet (reaction I) and trip...
  
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Beilstein J. Org. Chem. 2018, 14, 2250–2258, doi:10.3762/bjoc.14.200

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Coordination-driven self-assembly of discrete Ru₆–Pt₆ prismatic cages

Aderonke Ajibola Adeyemo and
Partha Sarathi Mukherjee

Full Research Paper
Published 27 Aug 2018

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Album
1. Graphical Abstract
2. Scheme 1: Self-assembly of the heterometallic prismatic cages.
  
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3. Scheme 2: Synthesis of the platinum metalloligand 2.
  
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4. Figure 1: ¹H NMR of 3b in CD₃OD.
  
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5. Figure 2: UV–vis spectra of the metalloligand 2 and heterometallic prismatic cages 3a and 3b in methanol (1.0...
  
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6. Figure 3: ESIMS spectrum of 3a in methanol. Inset: experimentally observed isotopic distribution patterns of ...
  
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7. Figure 4: Energy-minimized structure of heterometallic trigonal prismatic cage 3a. Hydrogen atoms are omitted...
  
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