New substrates for Suzuki-Miyaura cross-coupling reactions

ORGN 734

Pierre-Luc Boudreault, pierre-luc.boudreault.1@ulaval.ca and Normand Voyer, normand.voyer@chm.ulaval.ca. Department of Chemistry and CREFSIP, Université Laval, Quebec City, QC G1K 7P4, Canada
The Suzuki reaction is widely used to synthesize polyolefins, styrenes, and substituted biphenyls. In part due to the stability, ease of preparation and low toxicity of the boronic acid compounds, there is currently widespread interest in applications of the Suzuki coupling, with new developments and refinements being reported constantly. In this context, we have prepared several 2-(aminomethyl)phenylboronic acid derivatives and study the influence of intramolecular interaction of the lone electron pair of the nitrogen with the empty p orbital of the boron atom on Suzuki cross-couplig reaction. The N-B interaction have been studied by X-ray crystallography and 11B NMR. Reaction of these substrates with differents aryl halides allows the efficient synthesis of o-aminomethylbiphenyl derivatives found in many natural and bioactive compounds.