Ayeni Deborah O, Mandal Samir K, Zajc Barbara
Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, NY 10031-9198.
Tetrahedron Lett. 2013 Nov 6;54(45):6008-6011. doi: 10.1016/j.tetlet.2013.08.069.
A Julia-Kocienski approach to trifluoromethyl-substituted alkenes was evaluated in the reactions of 1,3-benzothiazol-2-yl, 1-phenyl-1-tetrazol-5-yl, and 1-butyl-1-tetrazol-5-yl 2,2,2-trifluoroethyl sulfones with aldehydes. Among the various conditions tested, the best yields were obtained with 1-phenyl-1-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.
在1,3-苯并噻唑-2-基、1-苯基-1-四氮唑-5-基和1-丁基-1-四氮唑-5-基2,2,2-三氟乙基砜与醛的反应中，评估了一种用于三氟甲基取代烯烃的Julia-Kocienski方法。在测试的各种条件中，使用1-苯基-1-四氮唑-5-基2,2,2-三氟乙基砜，在CsF介导的、室温下于DMSO中的烯烃化反应中获得了最佳产率。芳香醛以23% - 86%的产率得到（三氟甲基）乙烯基衍生物，立体选择性一般中等。Julia-Kocienski试剂的直接合成以及在温和反应条件下转化为三氟甲基取代的烯烃是该方法的优点。
