Literature DB >> 12354008

Mild and efficient aryl-alkenyl coupling via Pd(II) catalysis in the presence of oxygen or Cu(II) oxidants.

Jay P Parrish1, Young Chun Jung, Seung Il Shin, Kyung Woon Jung.   

Abstract

We report herein a mild and efficient method for carbon-carbon bond formation between aryl stannanes and olefins via Pd(II) catalysis in the presence of oxygen or Cu(II) oxidants as a reoxidant. The process allows reactions between various olefins and aryl stannanes of varying electron density. Coupling methods under these oxidation conditions are comparatively described, and the benefits and limitations are also discussed.

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Year:  2002        PMID: 12354008     DOI: 10.1021/jo020159p

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  17 in total

1.  Pd(II)-catalyzed oxidative 1,1-diarylation of terminal olefins.

Authors:  Erik W Werner; Kaveri B Urkalan; Matthew S Sigman
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

2.  Palladium-Catalyzed 1,3-Difunctionalization Using Terminal Alkenes with Alkenyl Nonaflates and Aryl Boronic Acids.

Authors:  Matthew S McCammant; Takashi Shigeta; Matthew S Sigman
Journal:  Org Lett       Date:  2016-03-28       Impact factor: 6.005

Review 3.  Bystanding F+ oxidants enable selective reductive elimination from high-valent metal centers in catalysis.

Authors:  Keary M Engle; Tian-Sheng Mei; Xisheng Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-24       Impact factor: 15.336

4.  Operationally simple and highly (E)-styrenyl-selective Heck reactions of electronically nonbiased olefins.

Authors:  Erik W Werner; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2011-06-06       Impact factor: 15.419

5.  Palladium-catalyzed 1,1-aryloxygenation of terminal olefins.

Authors:  Andrew D Satterfield; Asako Kubota; Melanie S Sanford
Journal:  Org Lett       Date:  2011-02-03       Impact factor: 6.005

6.  A highly selective and general palladium catalyst for the oxidative Heck reaction of electronically nonbiased olefins.

Authors:  Erik W Werner; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

7.  Anti-Markovnikov hydroalkylation of allylic amine derivatives via a palladium-catalyzed reductive cross-coupling reaction.

Authors:  Ryan J DeLuca; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2011-07-11       Impact factor: 15.419

8.  Palladium-Catalyzed Enantioselective Redox-Relay Heck Arylation of 1,1-Disubstituted Homoallylic Alcohols.

Authors:  Zhi-Min Chen; Margaret J Hilton; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-09-01       Impact factor: 15.419

9.  Oxidative Heck vinylation for the synthesis of complex dienes and polyenes.

Authors:  Jared H Delcamp; Paul E Gormisky; M Christina White
Journal:  J Am Chem Soc       Date:  2013-05-30       Impact factor: 15.419

10.  Enantioselective redox-relay oxidative heck arylations of acyclic alkenyl alcohols using boronic acids.

Authors:  Tian-Sheng Mei; Erik W Werner; Alexander J Burckle; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2013-04-24       Impact factor: 15.419

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