Literature DB >> 32203638

Gold-Catalyzed 1,2-Diarylation of Alkenes.

Chetan C Chintawar1, Amit K Yadav1, Nitin T Patil1.   

Abstract

Herein, we disclose the gold-catalyzed 1,2-diarylation of alkenes through the interplay of ligand-enabled AuI /AuIII catalysis with the idiosyncratic π-activation mode of gold complexes. Unlike the classical migratory-insertion-based approach to 1,2-diarylation, the present approach not only circumvents the formation of direct Ar-Ar' coupling and Heck-type side products but more intriguingly demonstrates reactivity and selectivity complementary to those of previously known metal catalysis (Pd, Ni, or Cu). Detailed investigations to underpin the mechanistic scenario revealed oxidative addition of aryl iodides to an AuI complex to be the rate-limiting step owing to the non-innocent nature of the aryl alkene.
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  1,2-difunctionalization; alkenes; cross-coupling; gold catalysis; π-activation

Year:  2020        PMID: 32203638     DOI: 10.1002/anie.202002141

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


  5 in total

1.  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

2.  Chiral Hemilabile P,N-Ligand-Assisted Gold Redox Catalysis for Enantioselective Alkene Aminoarylation.

Authors:  Xiaohan Ye; Chenhuan Wang; Shuyao Zhang; Qi Tang; Lukasz Wojtas; Minyong Li; Xiaodong Shi
Journal:  Chemistry       Date:  2022-05-11       Impact factor: 5.020

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

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

4.  Hemilabile MIC^N ligands allow oxidant-free Au(i)/Au(iii) arylation-lactonization of γ-alkenoic acids.

Authors:  Pau Font; Hugo Valdés; Gregorio Guisado-Barrios; Xavi Ribas
Journal:  Chem Sci       Date:  2022-07-22       Impact factor: 9.969

5.  A Systematic Study of the Effects of Complex Structure on Aryl Iodide Oxidative Addition at Bipyridyl-Ligated Gold(I) Centers.

Authors:  Jamie A Cadge; John F Bower; Christopher A Russell
Journal:  Angew Chem Int Ed Engl       Date:  2021-10-18       Impact factor: 16.823

  5 in total

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