Palladium-Catalyzed Alkylation of sp² and sp³ C−H Bonds with Methylboroxine and Alkylboronic Acids:  Two Distinct C−H Activation Pathways

Abstract

Palladium-catalyzed alkylations of sp2 and sp3 C-H bonds with either methylboroxine or alkylboronic acids were developed. Ag2O or AgCO3 is used as a crucial oxidant and promoter for the transmetalation step. Ether, ester, alcohol, and alkene functional groups are tolerated. A new C-H activation pathway differing from the cyclometalation process is elucidated using methylboroxine as the coupling partner.