α-Arylation of Silyl Enol Ethers via Rhodium(III)-Catalyzed C–H Functionalization
Xuezhen Kou, Kevin G. M. Kou
Abstract
Carbon–hydrogen (C–H) bond functionalization streamlines synthesis by increasing step- and atom-economies. This approach, catalyzed by Rh(III), is combined with the α-arylation of ketone-derived silyl enol ethers to achieve a direct cross-coupling event. The advancement of electron-rich alkenes as substrates is enabled through the use of a silver additive and complements existing C–H activation methods that transform enol ester derivatives and electron-deficient alkenes. A Rh(III)/(V)/(III) catalytic cycle is proposed to rationalize mechanistic observations.
Topics & Concepts
EnolSilylationCatalysisChemistrySurface modificationRhodiumKetoneCatalytic cycleAtom economyOrganic chemistryCombinatorial chemistryMedicinal chemistryPhysical chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis