title: Julia-Kocienski Approach to Trifluoromethyl-Substituted Alkenes1.
abstract: A Julia-Kocienski approach to trifluoromethyl-substituted alkenes was evaluated in the reactions of 1,3-benzothiazol-2-yl, 1-phenyl-1H-tetrazol-5-yl, and 1-tbutyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfones with aldehydes. Among the various conditions tested, the best yields were obtained with 1-phenyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfone, in CsF-mediated, room temperature olefinations in DMSO. Aromatic aldehydes gave (trifluoromethyl)vinyl derivatives in 23-86% yields, with generally moderate stereoselectivity. Straightforward synthesis of the Julia-Kocienski reagent, and conversion to trifluoromethyl-substituted alkenes under mild reaction conditions, are the advantages of this approach.
authors.affiliation: Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, NY 10031-9198.
authors.forename: Deborah O
authors.initials: DO
authors.lastname: Ayeni
authors.affiliation: Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, NY 10031-9198.
authors.forename: Samir K
authors.initials: SK
authors.lastname: Mandal
authors.affiliation: Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, NY 10031-9198.
authors.forename: Barbara
authors.initials: B
authors.lastname: Zajc