Stereospecific Pd-Catalyzed Cross-Coupling Reactions of Secondary Alkylboron Nucleophiles and Aryl Chlorides

Authors

Ling Li, CUNY City College
Shibin Zhao, CUNY Graduate Center
Amruta Joshi-Pangu, CUNY Graduate Center
Mohamed Diane, CUNY City College
Mark R. Biscoe, CUNY City CollegeFollow

Document Type

Article

Publication Date

September 2015

Abstract

We report the development of a Pd-catalyzed process for the stereospecific cross-coupling of unactivated secondary alkylboron nucleophiles and aryl chlorides. This process tolerates the use of secondary alkylboronic acids and secondary alkyltrifluoroborates and occurs without significant isomerization of the alkyl nucelophile. Optically active secondary alkyltrifluoroborate reagents undergo cross-coupling reactions with stereospecific inversion of configuration using this method.

Comments

This work was originally published in Journal of the American Chemical Society, available at doi:10.1021/ja508815w.