Literature DB >> 20858011

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

Erik W Werner1, Matthew S Sigman.   

Abstract

A general, highly selective oxidative Heck reaction is reported. The reaction is high-yielding under mild conditions without the need for base or high temperatures, and the selectivity is excellent, without the requirement for electronically biased olefins or other specific directing groups. A preliminary mechanistic investigation suggests that the unusually high selectivity may be due to the catalyst's sensitivity to C-H bond strength in the selectivity-determining β-hydride elimination step.

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Year:  2010        PMID: 20858011      PMCID: PMC3011814          DOI: 10.1021/ja1060998

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  13 in total

1.  Substituent Effects on the C-H Bond Dissociation Energy of Toluene. A Density Functional Study.

Authors:  Yun-Dong Wu; Chui-Ling Wong; Kyle W. K. Chan; Guo-Zhen Ji; Xi-Kui Jiang
Journal:  J Org Chem       Date:  1996-01-26       Impact factor: 4.354

2.  Pd(OAc)(2) catalyzed olefination of highly electron-deficient perfluoroarenes.

Authors:  Xingang Zhang; Shilu Fan; Chun-Yang He; Xiaolong Wan; Qiao-Qiao Min; Jie Yang; Zhong-Xing Jiang
Journal:  J Am Chem Soc       Date:  2010-04-07       Impact factor: 15.419

3.  Mizoroki-Heck type reaction of organoboron reagents with alkenes and alkynes. A Pd(II)-catalyzed pathway with Cu(OAc)2 as an oxidant.

Authors:  X Du; M Suguro; K Hirabayashi; A Mori; T Nishikata; N Hagiwara; K Kawata; T Okeda; H F Wang; K Fugami; M Kosugi
Journal:  Org Lett       Date:  2001-10-18       Impact factor: 6.005

4.  Efficient activation of aromatic C-H bonds for addition to C-C multiple bonds

Authors: 
Journal:  Science       Date:  2000-03-17       Impact factor: 47.728

5.  Oxidative palladium(II) catalysis: A highly efficient and chemoselective cross-coupling method for carbon-carbon bond formation under base-free and nitrogenous-ligand conditions.

Authors:  Kyung Soo Yoo; Cheol Hwan Yoon; Rajesh K Mishra; Young Chun Jung; Sung Wook Yi; Kyung Woon Jung
Journal:  J Am Chem Soc       Date:  2006-12-20       Impact factor: 15.419

6.  Pd(II)-catalyzed olefination of electron-deficient arenes using 2,6-dialkylpyridine ligands.

Authors:  Yang-Hui Zhang; Bing-Feng Shi; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2009-04-15       Impact factor: 15.419

7.  Dioxygen-promoted regioselective oxidative heck arylations of electron-rich olefins with arylboronic acids.

Authors:  Murugaiah M S Andappan; Peter Nilsson; Henrik von Schenck; Mats Larhed
Journal:  J Org Chem       Date:  2004-08-06       Impact factor: 4.354

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

Authors:  Jay P Parrish; Young Chun Jung; Seung Il Shin; Kyung Woon Jung
Journal:  J Org Chem       Date:  2002-10-04       Impact factor: 4.354

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

Authors:  Young Chun Jung; Rajesh Kumar Mishra; Cheol Hwan Yoon; Kyung Woon Jung
Journal:  Org Lett       Date:  2003-06-26       Impact factor: 6.005

10.  Palladium-catalyzed oxidative intermolecular difunctionalization of terminal alkenes with organostannanes and molecular oxygen.

Authors:  Kaveri Balan Urkalan; Matthew S Sigman
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

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  25 in total

1.  Palladium-catalyzed regio- and stereoselective γ-arylation of tertiary allylic amines: identification of potent adenylyl cyclase inhibitors.

Authors:  Zhishi Ye; Tarsis F Brust; Val J Watts; Mingji Dai
Journal:  Org Lett       Date:  2015-02-10       Impact factor: 6.005

2.  Sequential allylic C-H amination/vinylic C-H arylation: a strategy for unnatural amino acid synthesis from α-olefins.

Authors:  Chao Jiang; Dustin J Covell; Antonia F Stepan; Mark S Plummer; M Christina White
Journal:  Org Lett       Date:  2012-02-24       Impact factor: 6.005

3.  Imparting catalyst control upon classical palladium-catalyzed alkenyl C-H bond functionalization reactions.

Authors:  Matthew S Sigman; Erik W Werner
Journal:  Acc Chem Res       Date:  2011-11-23       Impact factor: 22.384

4.  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

5.  Enantioselective Heck arylations of acyclic alkenyl alcohols using a redox-relay strategy.

Authors:  Erik W Werner; Tian-Sheng Mei; Alexander J Burckle; Matthew S Sigman
Journal:  Science       Date:  2012-12-14       Impact factor: 47.728

6.  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

7.  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

8.  Aerobic oxidative Heck/dehydrogenation reactions of cyclohexenones: efficient access to meta-substituted phenols.

Authors:  Yusuke Izawa; Changwu Zheng; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-19       Impact factor: 15.336

9.  A Diverted Aerobic Heck Reaction Enables Selective 1,3-Diene and 1,3,5-Triene Synthesis through C-C Bond Scission.

Authors:  Neil J McAlpine; Long Wang; Brad P Carrow
Journal:  J Am Chem Soc       Date:  2018-10-15       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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