Three-Component Ru-Catalyzed Regioselective Alkylarylation of Vinylarenes via <i>Meta</i>-Selective C(sp<sup>2</sup>)–H Bond Functionalization
Hongchao Liu, Xiao-Ping Gong, Yu‐Zhao Wang, Zhi‐Jie Niu, Heng Yue, Xue‐Yuan Liu, Yong‐Min Liang
Abstract
We report a novel Ru-catalyzed regioselective alkylarylation of vinylarenes with alkyl halides and arenes via meta-C(sp2)–H bond functionalization to construct 1,1-diarylalkanes that generally show bioactivity. In this transformation, a wide spectrum of primary, secondary, and tertiary alkyl halides and electronically varied arenes was well-tolerated. This reaction is characterized by its exquisite regioselectivity of vinylarenes, unique meta-C(sp2)–H selectivity, and redox-neutral conditions. The mechanism presented was supported by radical probes and kinetic isotope effect studies.
Topics & Concepts
RegioselectivityChemistryAlkylHalideSurface modificationCatalysisSelectivityKinetic isotope effectCombinatorial chemistryMedicinal chemistryStereochemistryOrganic chemistryDeuteriumPhysical chemistryPhysicsQuantum mechanicsCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCatalytic Cross-Coupling Reactions