Anti-Markovnikov hydroallylation reaction of alkenes via scandium-catalyzed allylic C‒H activation
Shiyu Wang, Lichao Ning, Tao Mao, Yuqiao Zhou, Maoping Pu, Xiaoming Feng, Shunxi Dong
Abstract
‒H activation pathway initiated by site-selective deprotonation with the assistance of cationic imidazolin-2-iminato scandium alkyl species followed by alkene insertion into the resulting scandium-allyl bond. A catalytic amount of Lewis base additives, such as amine and tetrahydrofuran (THF) show significant effects on the reactivity and E/Z selectivity. The reaction mechanism is elucidated by experimental studies and theoretical calculations.
Topics & Concepts
ChemistryAllylic rearrangementAlkeneMarkovnikov's ruleMedicinal chemistryCationic polymerizationDeprotonationScandiumCatalysisAlkylArylLewis acids and basesCombinatorial chemistryOrganic chemistryRegioselectivityIonCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsSynthesis and Catalytic Reactions