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

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.