Literature DB >> 35368720

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

R Tyler Mertens1, Charles E Greif1, James T Coogle1, Gilles Berger2, Sean Parkin1, Mark D Watson1, Samuel G Awuah1,3.   

Abstract

The development of oxidant-free gold-catalyzed cross coupling reactions involving aryl halides have been hamstrung by the lack of gold catalysts capable of performing oxidative addition at Au(I) centers. Herein, we report the development of novel tricoordinate Au(I) catalysts supported by N,N-bidentate ligands and ligated by phosphine or arsine ligands for C-H functionalization without external oxidants to form biaryls with no homocoupling. The unsymmetrical character of the Au(I) catalyst is critical to facilitating this necessary orthogonal transformation. This study unveils yet another potential of Au(I) catalysis in biaryl synthesis.

Entities:  

Keywords:  C-H activation; Oxidative addition; gold catalysis; tricoordinate gold

Year:  2022        PMID: 35368720      PMCID: PMC8975124          DOI: 10.1016/j.jcat.2022.02.019

Source DB:  PubMed          Journal:  J Catal        ISSN: 0021-9517            Impact factor:   7.920


  46 in total

1.  Gold-catalyzed ethynylation of arenes.

Authors:  Teresa de Haro; Cristina Nevado
Journal:  J Am Chem Soc       Date:  2010-02-10       Impact factor: 15.419

Review 2.  Dinuclear gold catalysis.

Authors:  Wenliang Wang; Cheng-Long Ji; Kai Liu; Chuan-Gang Zhao; Weipeng Li; Jin Xie
Journal:  Chem Soc Rev       Date:  2020-12-14       Impact factor: 54.564

3.  Trans Influence of Ligands on the Oxidation of Gold(I) Complexes.

Authors:  Yangyang Yang; Lukas Eberle; Florian F Mulks; Jonas F Wunsch; Marc Zimmer; Frank Rominger; Matthias Rudolph; A Stephen K Hashmi
Journal:  J Am Chem Soc       Date:  2019-10-16       Impact factor: 15.419

4.  Au-Catalyzed Biaryl Coupling To Generate 5- to 9-Membered Rings: Turnover-Limiting Reductive Elimination versus π-Complexation.

Authors:  Tom J A Corrie; Liam T Ball; Christopher A Russell; Guy C Lloyd-Jones
Journal:  J Am Chem Soc       Date:  2016-12-29       Impact factor: 15.419

5.  Gold-Catalyzed C(sp2 )-C(sp) Coupling by Alkynylation through Oxidative Addition of Bromoalkynes.

Authors:  Yangyang Yang; Jasmin Schießl; Sirine Zallouz; Verena Göker; Jürgen Gross; Matthias Rudolph; Frank Rominger; A Stephen K Hashmi
Journal:  Chemistry       Date:  2019-06-26       Impact factor: 5.236

6.  Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands.

Authors:  Ruben Martin; Stephen L Buchwald
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

7.  Au(i)/Au(iii)-Catalyzed C-N coupling.

Authors:  Jessica Rodriguez; Nicolas Adet; Nathalie Saffon-Merceron; Didier Bourissou
Journal:  Chem Commun (Camb)       Date:  2019-12-02       Impact factor: 6.222

8.  Exceptionally fast carbon-carbon bond reductive elimination from gold(III).

Authors:  William J Wolf; Matthew S Winston; F Dean Toste
Journal:  Nat Chem       Date:  2013-12-22       Impact factor: 24.427

9.  Stable gold(III) catalysts by oxidative addition of a carbon-carbon bond.

Authors:  Chung-Yeh Wu; Takahiro Horibe; Christian Borch Jacobsen; F Dean Toste
Journal:  Nature       Date:  2015-01-22       Impact factor: 49.962

10.  Rational development of catalytic Au(I)/Au(III) arylation involving mild oxidative addition of aryl halides.

Authors:  Abdallah Zeineddine; Laura Estévez; Sonia Mallet-Ladeira; Karinne Miqueu; Abderrahmane Amgoune; Didier Bourissou
Journal:  Nat Commun       Date:  2017-09-18       Impact factor: 14.919

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