N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings
Author(s)Bruno, Nicholas C.; Niljianskul, Nootaree; Buchwald, Stephen Leffler
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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 −NH[subscript 2] 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.
DepartmentMassachusetts Institute of Technology. Department of Chemistry
The Journal of Organic Chemistry
Bruno, Nicholas C., Nootaree Niljianskul, and Stephen L. Buchwald. “N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings.” The Journal of Organic Chemistry 79, no. 9 (May 2, 2014): 4161–4166. © 2014 American Chemical Society
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