Migratory Insertion of CO into a Au-C Bond

Jamie A Cadge; Paul J Gates; John F Bower; Christopher A Russell

doi:10.1021/jacs.2c10432

Migratory Insertion of CO into a Au-C Bond

Jamie A Cadge, Paul J Gates, John F Bower^*, Christopher A Russell^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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Abstract

A MeDalPhos-ligated gold(III) metallafluorene complex, generated via C-C oxidative addition of biphenylene, reacts with CO to produce 9-fluorenone. Experimental and computational studies show that this proceeds via a hitherto unknown migratory insertion of CO into a Au(III)-C bond. This process is more energetically challenging compared to other M-C bonds, but once achieved, the product is comparatively stable with respect to retro-carbonylation. Exploiting migratory insertion of CO into Au-C bonds may extend the range of products that are accessible using gold chemistry.

Original language	English
Pages (from-to)	19719-19725
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	144
Issue number	43
Early online date	25 Oct 2022
DOIs	https://doi.org/10.1021/jacs.2c10432
Publication status	Published - 2 Nov 2022

Bibliographical note

Funding Information:
We thank the Bristol Chemical Synthesis Centre for Doctoral Training, funded by the EPSRC (EP/L015366/1) and the University of Bristol (studentship to J.A.C.) for funding. We thank Dr. Natalie Fey (Bristol) for advice with computation and the generous donation of CO. We thank Prof. Craig Butts and Paul Lawrence (Bristol) for their assistance with NMR spectroscopy. We thank Dr. Natalie Pridmore (Bristol) for assistance with X-ray crystallography. 13

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title = "Migratory Insertion of CO into a Au-C Bond",

abstract = "A MeDalPhos-ligated gold(III) metallafluorene complex, generated via C-C oxidative addition of biphenylene, reacts with CO to produce 9-fluorenone. Experimental and computational studies show that this proceeds via a hitherto unknown migratory insertion of CO into a Au(III)-C bond. This process is more energetically challenging compared to other M-C bonds, but once achieved, the product is comparatively stable with respect to retro-carbonylation. Exploiting migratory insertion of CO into Au-C bonds may extend the range of products that are accessible using gold chemistry.",

author = "Cadge, {Jamie A} and Gates, {Paul J} and Bower, {John F} and Russell, {Christopher A}",

note = "Funding Information: We thank the Bristol Chemical Synthesis Centre for Doctoral Training, funded by the EPSRC (EP/L015366/1) and the University of Bristol (studentship to J.A.C.) for funding. We thank Dr. Natalie Fey (Bristol) for advice with computation and the generous donation of CO. We thank Prof. Craig Butts and Paul Lawrence (Bristol) for their assistance with NMR spectroscopy. We thank Dr. Natalie Pridmore (Bristol) for assistance with X-ray crystallography. 13 Publisher Copyright: {\textcopyright} ",

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month = nov,

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doi = "10.1021/jacs.2c10432",

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AU - Cadge, Jamie A

AU - Gates, Paul J

AU - Bower, John F

AU - Russell, Christopher A

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PY - 2022/11/2

Y1 - 2022/11/2

N2 - A MeDalPhos-ligated gold(III) metallafluorene complex, generated via C-C oxidative addition of biphenylene, reacts with CO to produce 9-fluorenone. Experimental and computational studies show that this proceeds via a hitherto unknown migratory insertion of CO into a Au(III)-C bond. This process is more energetically challenging compared to other M-C bonds, but once achieved, the product is comparatively stable with respect to retro-carbonylation. Exploiting migratory insertion of CO into Au-C bonds may extend the range of products that are accessible using gold chemistry.

AB - A MeDalPhos-ligated gold(III) metallafluorene complex, generated via C-C oxidative addition of biphenylene, reacts with CO to produce 9-fluorenone. Experimental and computational studies show that this proceeds via a hitherto unknown migratory insertion of CO into a Au(III)-C bond. This process is more energetically challenging compared to other M-C bonds, but once achieved, the product is comparatively stable with respect to retro-carbonylation. Exploiting migratory insertion of CO into Au-C bonds may extend the range of products that are accessible using gold chemistry.

U2 - 10.1021/jacs.2c10432

DO - 10.1021/jacs.2c10432

M3 - Article (Academic Journal)

C2 - 36282061

SN - 0002-7863

VL - 144

SP - 19719

EP - 19725

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 43

ER -

Migratory Insertion of CO into a Au-C Bond

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