title: Formal Allylic C(sp3)-H Bond Activation of Alkenes Triggered by a Sodium Amide.
abstract: The catalytic use of a sodium amide has been exploited for formal allylic C(sp3)-H bond activation of alkenes under mild conditions. Subsequent C-C bond formations with imines have proceeded in high yields with complete regioselectivity and excellent geometric selectivity. Aromatic cyano, chloro, and bromo functionalities are tolerated by the transition metal-free catalyst. Complex amines bearing a C═C double bond and distinct heteroaromatic units have been prepared in a single step. The critical importance of sodium versus other s-, p-, d-, and f-block metals as well as metal-free systems has been revealed. In addition, two catalytically active sodium-based intermediates were detected by NMR and HRMS analyses.
authors.affiliation: EaStCHEM School of Chemistry, The University of Edinburgh , The King's Buildings, David Brewster Road, Edinburgh EH9 3FJ, U.K.
authors.forename: Wei
authors.initials: W
authors.lastname: Bao
authors.affiliation: EaStCHEM School of Chemistry, The University of Edinburgh , The King's Buildings, David Brewster Road, Edinburgh EH9 3FJ, U.K.
authors.forename: Hanno
authors.initials: H
authors.lastname: Kossen
authors.affiliation: EaStCHEM School of Chemistry, The University of Edinburgh , The King's Buildings, David Brewster Road, Edinburgh EH9 3FJ, U.K.
authors.forename: Uwe
authors.identifier: 0000-0002-9145-6219
authors.initials: U
authors.lastname: Schneider