C-C coupling reactivity of an alkylgold(III) fluoride complex with arylboronic acids.
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.
Mankad
Neal P
NP
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Toste
F Dean
FD
D001897:Boronic Acids / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*
D001897:Boronic Acids; D009942:Organometallic Compounds; D002244:Carbon; D006046:Gold