Literature DB >> 20111778

Intermolecular oxidative cross-coupling of arenes.

James A Ashenhurst1.   

Abstract

Biaryls constitute an important subunit found in medicinal agents, functional materials, and natural products. While the Suzuki reaction and related processes currently represent the method of choice for the construction of arene-arene bonds, the direct-coupling of two unfunctionalized arenes mediated by the addition of an oxidant represents a powerful alternative strategy for biaryl synthesis. This tutorial review describes recent progress in this rapidly developing field, focusing on intermolecular examples of selective arene oxidation strategies and metal-catalyzed oxidative cross-coupling via C-H activation.

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Year:  2009        PMID: 20111778     DOI: 10.1039/b907809f

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  30 in total

1.  Synthesis of unsymmetrical o-biphenols and o-binaphthols via silicon-tethered Pd-catalyzed C-H arylation.

Authors:  Chunhui Huang; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

2.  Direct stereoselective α-arylation of unmodified enals using an organocatalytic cross-coupling-like reaction.

Authors:  Xixi Song; Aiguo Song; Fang Zhang; He-Xing Li; Wei Wang
Journal:  Nat Commun       Date:  2011-11-08       Impact factor: 14.919

3.  A facile, metal- and solvent-free, autoxidative coupling of quinolines with indoles and pyrroles.

Authors:  Mikaël Brasse; Jonathan A Ellman; Robert G Bergman
Journal:  Chem Commun (Camb)       Date:  2011-03-29       Impact factor: 6.222

4.  Silanol: a traceless directing group for Pd-catalyzed o-alkenylation of phenols.

Authors:  Chunhui Huang; Buddhadeb Chattopadhyay; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2011-07-21       Impact factor: 15.419

5.  Double-fold C-H oxygenation of arenes using PyrDipSi: a general and efficient traceless/modifiable silicon-tethered directing group.

Authors:  Anton V Gulevich; Ferdinand S Melkonyan; Dhruba Sarkar; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2012-03-19       Impact factor: 15.419

6.  Pd-catalyzed modifiable silanol-directed aromatic C-H oxygenation.

Authors:  Chunhui Huang; Nugzar Ghavtadze; Benhur Godoi; Vladimir Gevorgyan
Journal:  Chemistry       Date:  2012-07-02       Impact factor: 5.236

7.  Nature-inspired stereospecific total synthesis of P-(+)-dispegatrine and four other monomeric sarpagine indole alkaloids.

Authors:  Chitra R Edwankar; Rahul V Edwankar; Jeffrey R Deschamps; James M Cook
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-16       Impact factor: 15.336

8.  The Pyridyldiisopropylsilyl Group: A Masked Functionality and Directing Group for Monoselective ortho-Acyloxylation and ortho-Halogenation Reactions of Arenes.

Authors:  Chunhui Huang; Natalia Chernyak; Alexander S Dudnik; Vladimir Gevorgyan
Journal:  Adv Synth Catal       Date:  2011-05-01       Impact factor: 5.837

9.  Practical Organocatalytic Synthesis of Functionalized Non-C2-Symmetrical Atropisomeric Biaryls.

Authors:  Hongyin Gao; Qing-Long Xu; Craig Keene; Muhammed Yousufuddin; Daniel H Ess; László Kürti
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-23       Impact factor: 15.336

10.  Studies on a biomimetic oxidative dimerization approach to the hibarimicins.

Authors:  Ian M Romaine; Gary A Sulikowski
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

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