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C-C coupling reactivity of an alkylgold(III) fluoride complex with arylboronic acids. | LitMetric

C-C coupling reactivity of an alkylgold(III) fluoride complex with arylboronic acids.

J Am Chem Soc

Department of Chemistry, University of California, Berkeley, California 94720, USA.

Published: September 2010

AI Article Synopsis

Article Abstract

Previously, alkylgold(III) fluorides have been proposed as catalytic intermediates that undergo C-C coupling with reagents such as arylboronic acids in Au(I)/Au(III) cross-coupling reactions. Here is reported the first experimental evidence for this elementary mechanistic step. Complexes of the type (NHC)AuMe (NHC = N-heterocyclic carbene) were oxidized with XeF(2) to yield cis-(NHC)AuMeF(2) products, which were found to be in equilibrium with their fluoride-dissociated, dimeric [(NHC)AuMe(μ-F)](2)[F](2) forms. In one case, a monomeric cis-(NHC)AuMeF(2) complex was favored exclusively in solution, and it was found to react with a variety of ArB(OH)(2) reagents to yield Ar-CH(3) products.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2939925PMC
http://dx.doi.org/10.1021/ja106257nDOI Listing

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