Literature DB >> 12816416

Oxygen-promoted Pd(II) catalysis for the coupling of organoboron compounds and olefins.

Young Chun Jung1, Rajesh Kumar Mishra, Cheol Hwan Yoon, Kyung Woon Jung.   

Abstract

Reported herein is a mild and efficient Pd(II) catalysis, leading to the formation of carbon-carbon bonds between a broad spectrum of organoboron compounds and alkenes. Molecular oxygen was employed to reoxidize the resultant Pd(0) species back to Pd(II) during catalytic cycles. This oxygen protocol promoted the desired Pd(II) catalysis, whereas it retarded competing Pd(0) catalytic pathways such as Heck or Suzuki couplings. [reaction: see text]

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Year:  2003        PMID: 12816416     DOI: 10.1021/ol034458s

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  19 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

3.  Catalyst-controlled regioselectivity in the synthesis of branched conjugated dienes via aerobic oxidative Heck reactions.

Authors:  Changwu Zheng; Dian Wang; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2012-09-28       Impact factor: 15.419

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.  Recent advancements and challenges of palladium(II)-catalyzed oxidation reactions with molecular oxygen as the sole oxidant.

Authors:  Keith M Gligorich; Matthew S Sigman
Journal:  Chem Commun (Camb)       Date:  2009-05-14       Impact factor: 6.222

6.  Transition State Force Field for the Asymmetric Redox-Relay Heck Reaction.

Authors:  Anthony R Rosales; Sean P Ross; Paul Helquist; Per-Ola Norrby; Matthew S Sigman; Olaf Wiest
Journal:  J Am Chem Soc       Date:  2020-05-14       Impact factor: 15.419

7.  Chemoselective Three-Component Coupling via A Tandem Pd Catalyzed Boron-Heck and Suzuki Reaction.

Authors:  Justin O'Neill; Kyung Soo Yoo; Kyung Woon Jung
Journal:  Tetrahedron Lett       Date:  2008-12-15       Impact factor: 2.415

8.  Asymmetric intermolecular boron Heck-type reactions via oxidative palladium(II) catalysis with chiral tridentate NHC-amidate-alkoxide ligands.

Authors:  Kyung Soo Yoo; Justin O'Neill; Satoshi Sakaguchi; Richard Giles; Joo Ho Lee; Kyung Woon Jung
Journal:  J Org Chem       Date:  2010-01-01       Impact factor: 4.354

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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