Chemoselective Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of (Diborylmethyl)silanes with Alkenyl Bromides

Abstract

Herein, we report the development of a palladium-catalyzed chemoselective cross-coupling of (diborylmethyl)silanes with alkenyl bromides. The reaction shows broad scope with respect to alkenyl bromides and (diborylmethyl)silanes, affording a range of alpha-silyl-substituted allylic boronate esters in good-to-excellent yields. The practicality of the developed coupling reaction is demonstrated by the gram-scale synthesis of alpha-silyl-substituted allylic boronate ester.