Room temperature hydroalkylation of electron-deficient olefins: sp3 C-H functionalization via a lewis acid-catalyzed intramolecular redox event.
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.
Pastine
Stefan J
SJ
Department of Chemistry, Columbia University, New York, New York 10027, USA.
McQuaid
Kevin M
KM
Sames
Dalibor
D
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
D000143:Acids; D000475:Alkenes; D002244:Carbon; D006859:Hydrogen