Literature DB >> 24799132

Gold-catalyzed allylation of aryl boronic acids: accessing cross-coupling reactivity with gold.

Mark D Levin1, F Dean Toste.   

Abstract

A sp(3)-sp(2) C-C cross-coupling reaction catalyzed by gold in the absence of a sacrificial oxidant is described. Vital to the success of this method is the implementation of a bimetallic catalyst bearing a bis(phosphino)amine ligand. A mechanistic hypothesis is presented, and observable transmetalation, C-Br oxidative addition, and C-C reductive elimination in a model gold complex are shown. We expect that this method will serve as a platform for the development of novel transformations involving redox-active gold catalysts.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CC coupling; allylation; bimetallic catalysis; gold catalysis; oxidative addition

Mesh:

Substances:

Year:  2014        PMID: 24799132      PMCID: PMC4076148          DOI: 10.1002/anie.201402924

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  30 in total

1.  Relativistic functional groups: aryl carbon-gold bond formation by selective transmetalation of boronic acids.

Authors:  David V Partyka; Matthias Zeller; Allen D Hunter; Thomas G Gray
Journal:  Angew Chem Int Ed Engl       Date:  2006-12-11       Impact factor: 15.336

2.  Gold-catalyzed organic reactions.

Authors:  A Stephen K Hashmi
Journal:  Chem Rev       Date:  2007-06-20       Impact factor: 60.622

3.  Gold-catalyzed homogeneous oxidative cross-coupling reactions.

Authors:  Guozhu Zhang; Yu Peng; Li Cui; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 4.  Cyclometalation using d-block transition metals: fundamental aspects and recent trends.

Authors:  Martin Albrecht
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

Review 5.  Gold and platinum catalysis--a convenient tool for generating molecular complexity.

Authors:  Alois Fürstner
Journal:  Chem Soc Rev       Date:  2009-07-22       Impact factor: 54.564

6.  Activation of aryl halides at gold(I): practical synthesis of (P,C) cyclometalated gold(III) complexes.

Authors:  Johannes Guenther; Sonia Mallet-Ladeira; Laura Estevez; Karinne Miqueu; Abderrahmane Amgoune; Didier Bourissou
Journal:  J Am Chem Soc       Date:  2014-01-23       Impact factor: 15.419

7.  A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  Synlett       Date:  2010-03-01       Impact factor: 2.454

8.  Gold-catalyzed three-component coupling: oxidative oxyarylation of alkenes.

Authors:  Asa D Melhado; William E Brenzovich; Aaron D Lackner; F Dean Toste
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

9.  Allylic substitution versus Suzuki cross-coupling: capitalizing on chemoselectivity with bifunctional substrates.

Authors:  Mahmud M Hussain; Patrick J Walsh
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-01       Impact factor: 15.336

10.  Au(I)/Au(III)-catalyzed Sonogashira-type reactions of functionalized terminal alkynes with arylboronic acids under mild conditions.

Authors:  Deyun Qian; Junliang Zhang
Journal:  Beilstein J Org Chem       Date:  2011-06-15       Impact factor: 2.883

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  26 in total

1.  Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant.

Authors:  Jin Wang; Chiyu Wei; Xuming Li; Pengyi Zhao; Chuan Shan; Lukasz Wojtas; Hao Chen; Xiaodong Shi
Journal:  Chemistry       Date:  2020-04-14       Impact factor: 5.236

2.  Facilitating Gold Redox Catalysis with Electrochemistry: An Efficient Chemical-Oxidant-Free Approach.

Authors:  Xiaohan Ye; Pengyi Zhao; Shuyao Zhang; Yanbin Zhang; Qilin Wang; Chuan Shan; Lukasz Wojtas; Hao Guo; Hao Chen; Xiaodong Shi
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-04       Impact factor: 15.336

3.  Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant.

Authors:  Jin Wang; Shuyao Zhang; Chang Xu; Lukasz Wojtas; Novruz G Akhmedov; Hao Chen; Xiaodong Shi
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-07       Impact factor: 15.336

4.  Gold redox catalysis for cyclization/arylation of allylic oximes: synthesis of isoxazoline derivatives.

Authors:  Abiola Azeez Jimoh; Seyedmorteza Hosseyni; Xiaohan Ye; Lukasz Wojtas; Yong Hu; Xiaodong Shi
Journal:  Chem Commun (Camb)       Date:  2019-07-09       Impact factor: 6.222

5.  Stable Au(I) catalysts for oxidant-free C-H Functionalization with Iodoarenes.

Authors:  R Tyler Mertens; Charles E Greif; James T Coogle; Gilles Berger; Sean Parkin; Mark D Watson; Samuel G Awuah
Journal:  J Catal       Date:  2022-02-28       Impact factor: 7.920

6.  Dinuclear Au(I), Au(II) and Au(III) Complexes with (CF2 )n Chains: Insights into The Role of Aurophilic Interactions in the Au(I) Oxidation.

Authors:  Alejandro Portugués; Delia Bautista; Juan Gil-Rubio
Journal:  Chemistry       Date:  2021-09-29       Impact factor: 5.020

7.  Homogeneous Gold Redox Chemistry: Organometallics, Catalysis, and Beyond.

Authors:  Banruo Huang; Mingyou Hu; F Dean Toste
Journal:  Trends Chem       Date:  2020-06-02

Review 8.  Homogeneous Gold-Catalyzed Oxidation Reactions.

Authors:  Zhitong Zheng; Xu Ma; Xinpeng Cheng; Ke Zhao; Kaylaa Gutman; Tianyou Li; Liming Zhang
Journal:  Chem Rev       Date:  2021-02-16       Impact factor: 72.087

9.  Halide-Dependent Mechanisms of Reductive Elimination from Gold(III).

Authors:  Matthew S Winston; William J Wolf; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-06-11       Impact factor: 15.419

10.  A dual catalytic strategy for carbon-phosphorus cross-coupling via gold and photoredox catalysis.

Authors:  Ying He; Hongmiao Wu; F Dean Toste
Journal:  Chem Sci       Date:  2015-02       Impact factor: 9.825

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