N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings
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Bruno-2014-N-substituted.pdf
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Author(s)
Bruno, Nicholas C.
Niljianskul, Nootaree
Buchwald, Stephen Leffler
Date Issued
April 2014
Journal
The Journal of Organic Chemistry
Citation
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
Version
Final published version
Abstract
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/jo500355k
