Scandium-Catalyzed Benzylic C(sp<sup>3</sup>)–H Alkenylation of Tertiary Anilines with Alkynes
Xian Xu, Xian Xu, Qianlin Sun, Xin Xu, Xin Xu
Abstract
This work describes the chemo- and stereoselective benzylic C(sp3)–H alkenylation of tertiary ortho-methyl anilines with internal alkynes using a simple β-diketiminato scandium catalyst. This protocol offers an efficient method for the synthesis of a new family of tertiary ortho-allylanilines in high yields. The resultant alkenylation products facilely underwent further chemical transformation to other valuable anilines. A cationic scandium benzyl species was isolated from a stoichiometric reaction and confirmed to be the catalytic intermediate.
Topics & Concepts
ScandiumChemistryCatalysisCationic polymerizationStereoselectivityStoichiometryMedicinal chemistryOrganic chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsSulfur-Based Synthesis Techniques