Open AccessMigratory Insertion of CO into a Au–C Bond
Author(s) -
Jamie A. Cadge,
Paul J. Gates,
John F. Bower,
Christopher A. Russell
Publication year - 2022
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.2c10432
Subject(s) - chemistry , biphenylene , migratory insertion , fluorenone , oxidative addition , carbonylation , crystallography , stereochemistry , catalysis , organic chemistry , carbon monoxide , polymer , phenylene , fluorene
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.