Palladium-Catalyzed Reductive Heck Hydroarylation of Unactivated Alkenes Using Hydrosilane at Room Temperature
Takahiro Shirai, Yusuke Migitera, Ryo Nakajima, Takuya Kumamoto
Abstract
The reductive Heck hydroarylation of unactivated alkenes has emerged as an essential reaction for regioselective hydroarylation. Herein, we report a palladium-catalyzed reductive Heck hydroarylation of unactivated alkenes under mild conditions with enhanced functional group tolerance using hydrosilane as the reducing reagent. Under the optimal conditions, the alkylarene yields increased, resulting in minimal undesired products. Mechanistic studies using deuterated reagents indicated the involvement of two competing catalytic cycles.
Topics & Concepts
ChemistryReagentRegioselectivityPalladiumCatalysisHeck reactionReductive eliminationOrganic chemistryCombinatorial chemistryFunctional groupPolymerCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis