Stable Au(I) catalysts for oxidant-free C-H functionalization with iodoarenes

R. Tyler Mertens; Charles E. Greif; James T. Coogle; Gilles Berger; Sean Parkin; Mark D. Watson; Samuel G. Awuah

doi:10.1016/j.jcat.2022.02.019

Stable Au(I) catalysts for oxidant-free C-H functionalization with iodoarenes

R. Tyler Mertens, Charles E. Greif, James T. Coogle, Gilles Berger, Sean Parkin, Mark D. Watson, Samuel G. Awuah

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

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.

Original language	English
Pages (from-to)	109-114
Number of pages	6
Journal	Journal of Catalysis
Volume	408
DOIs	https://doi.org/10.1016/j.jcat.2022.02.019
State	Published - Apr 2022

Bibliographical note

Publisher Copyright:
© 2022 Elsevier Inc.

Keywords

C-H activation
Gold catalysis
Oxidative addition
Tricoordinate gold

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry

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10.1016/j.jcat.2022.02.019

Cite this

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title = "Stable Au(I) catalysts for oxidant-free C-H functionalization with iodoarenes",

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.",

keywords = "C-H activation, Gold catalysis, Oxidative addition, Tricoordinate gold",

author = "Mertens, {R. Tyler} and Greif, {Charles E.} and Coogle, {James T.} and Gilles Berger and Sean Parkin and Watson, {Mark D.} and Awuah, {Samuel G.}",

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year = "2022",

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doi = "10.1016/j.jcat.2022.02.019",

language = "English",

volume = "408",

pages = "109--114",

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T1 - Stable Au(I) catalysts for oxidant-free C-H functionalization with iodoarenes

AU - Mertens, R. Tyler

AU - Greif, Charles E.

AU - Coogle, James T.

AU - Berger, Gilles

AU - Parkin, Sean

AU - Watson, Mark D.

AU - Awuah, Samuel G.

PY - 2022/4

Y1 - 2022/4

N2 - 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.

AB - 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.

KW - C-H activation

KW - Gold catalysis

KW - Oxidative addition

KW - Tricoordinate gold

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DO - 10.1016/j.jcat.2022.02.019

M3 - Article

AN - SCOPUS:85126705946

SN - 0021-9517

VL - 408

SP - 109

EP - 114

JO - Journal of Catalysis

JF - Journal of Catalysis

ER -

Stable Au(I) catalysts for oxidant-free C-H functionalization with iodoarenes

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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