title: Room temperature hydroalkylation of electron-deficient olefins: sp3 C-H functionalization via a lewis acid-catalyzed intramolecular redox event.
abstract: A practical method for the intramolecular hydroalkylation of electron-deficient olefins has been developed. The direct transformation of benzylic, tertiary, and sterically hindered secondary sp3 C-H bonds into C-C bonds under the action of a catalytic amount of a variety of Lewis acids is described. The mechanism of these transformations is proposed to involve a tandem hydride transfer/cyclization sequence.
authors.affiliation: Department of Chemistry, Columbia University, New York, New York 10027, USA.
authors.forename: Stefan J
authors.initials: SJ
authors.lastname: Pastine
authors.forename: Kevin M
authors.initials: KM
authors.lastname: McQuaid
authors.forename: Dalibor
authors.initials: D
authors.lastname: Sames
mesh_terms: D000143:Acids / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000478:Alkylation; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D004583:Electrons; D006859:Hydrogen / Q000737:chemistry*; D008956:Models, Chemical; D010084:Oxidation-Reduction; D013696:Temperature
chemical_list: D000143:Acids; D000475:Alkenes; D002244:Carbon; D006859:Hydrogen