Julia-Kocienski approach to trifluoromethyl-substituted alkenes

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• 作者：Deborah O. Ayeni ; Samir K. M ; al ; Barbara Zajc
• 关键词：Fluoroorganic ; Trifluoromethyl ; Olefination ; Julia&ndash ; Kocienski
• 刊名：Tetrahedron Letters
• 出版年：2013
• 出版时间：6 November, 2013
• 年：2013
• 卷：54
• 期：45
• 页码：6008-6011
• 全文大小：992 K

文摘

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.