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

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

Funding Information:
We are grateful to the University of Kentucky for funding. The authors acknowledge support of the Center for Pharmaceutical Research and Innovation (NIH P20 GM130456) and National Institutes of Health grant R01CA258421-01 (S.G.A.).

Funding Information:
The authors declare the following financial interests/personal relationships which may be considered as potential competing interests: Samuel G. Awuah reports financial support was provided by University of Kentucky. Samuel G. Awuah reports a relationship with University of Kentucky that includes: funding grants. Samuel G. Awuah has patent THREE-COORDINATE AU(I) PROBES AND USE IN SELECTIVELY DISRUPTING MITOCHONDRIA IN CANCER CELLS pending to University of Kentucky Research Foundation.

Funding Information:
We would like to thank all the facilities at the University of Kentucky who provided support in completion of the experiments detailed in this manuscript. The UK NMR Center supported by NSF (CHE997738) and the UK X-ray facility supported by the MRI program from NSF (CHE-1625732).

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.}",

note = "Funding Information: We are grateful to the University of Kentucky for funding. The authors acknowledge support of the Center for Pharmaceutical Research and Innovation (NIH P20 GM130456) and National Institutes of Health grant R01CA258421-01 (S.G.A.). Funding Information: The authors declare the following financial interests/personal relationships which may be considered as potential competing interests: Samuel G. Awuah reports financial support was provided by University of Kentucky. Samuel G. Awuah reports a relationship with University of Kentucky that includes: funding grants. Samuel G. Awuah has patent THREE-COORDINATE AU(I) PROBES AND USE IN SELECTIVELY DISRUPTING MITOCHONDRIA IN CANCER CELLS pending to University of Kentucky Research Foundation. Funding Information: We would like to thank all the facilities at the University of Kentucky who provided support in completion of the experiments detailed in this manuscript. The UK NMR Center supported by NSF (CHE997738) and the UK X-ray facility supported by the MRI program from NSF (CHE-1625732). Publisher Copyright: {\textcopyright} 2022 Elsevier Inc.",

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

language = "English",

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AU - Greif, Charles E.

AU - Coogle, James T.

AU - Berger, Gilles

AU - Parkin, Sean

AU - Watson, Mark D.

AU - Awuah, Samuel G.

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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.

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KW - Gold catalysis

KW - Oxidative addition

KW - Tricoordinate gold

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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