N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings
2014
Bruno, Nicholas C. | Niljianskul, Nootaree | Buchwald, Stephen L.
A series of phosphine-ligated palladium precatalysts based on N-methyl- and N-phenyl-2-aminobiphenyl have been developed. Substitution at the nitrogen center prevents the presence of traces of aminobiphenyls that contain a free −NH₂ group from contaminating cross-coupling products. These precatalysts produce N-substituted carbazoles upon activation, which cannot consume starting materials. These precatalysts were efficiently generated from 2-aminobiphenyl with minimal purification and found to be highly effective in Suzuki–Miyaura and C–N cross-coupling reactions.
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