title: Enantioselective C-H bond functionalization triggered by radical trifluoromethylation of unactivated alkene.
abstract: An asymmetric unactivated alkene/C-H bond difunctionalization reaction for the concomitant construction of C-CF3 and C-O bonds was realized by using a Cu/Brønsted acid cooperative catalytic system, thus providing facile access to valuable chiral CF3-containing N,O-aminals with excellent regio-, chemo-, and enantioselectivity. Mechanistic studies revealed that this reaction may proceed by an unprecedented 1,5-hydride shift involving activation of unactivated alkenes and a radical trifluoromethylation to initiate subsequent enantioselective functionalization of C-H bonds. Control experiments also suggested that chiral Brønsted acid plays multiple roles and not only controls the stereoselectivity but also increases the reaction rate through activation of Togni's reagent.
authors.affiliation: Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P. R. China).
authors.forename: Peng
authors.initials: P
authors.lastname: Yu
authors.forename: Jin-Shun
authors.initials: JS
authors.lastname: Lin
authors.forename: Lei
authors.initials: L
authors.lastname: Li
authors.forename: Sheng-Cai
authors.initials: SC
authors.lastname: Zheng
authors.forename: Ya-Ping
authors.initials: YP
authors.lastname: Xiong
authors.forename: Li-Jiao
authors.initials: LJ
authors.lastname: Zhao
authors.forename: Bin
authors.initials: B
authors.lastname: Tan
authors.forename: Xin-Yuan
authors.initials: XY
authors.lastname: Liu
keywords: CH activation; copper; enantioselectivity; radical chemistry; reaction mechanisms