芳醛的氧化 3,3,3-三氟丙基化反应。
Oxidative 3,3,3-trifluoropropylation of arylaldehydes.
机构信息
Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
出版信息
Beilstein J Org Chem. 2013 Nov 11;9:2417-21. doi: 10.3762/bjoc.9.279. eCollection 2013.
Abstract
A reaction between (E)-trimethyl(3,3,3-trifluoroprop-1-en-1-yl)silane (1) and arylaldehydes 2 was triggered by fluoride anions to afford aryl 3,3,3-trifluoropropyl ketones 3 in moderate to good yield. A mechanistic study of this reaction indicated that it occurred via an allyl alkoxide (4). A subsequent 1,3-proton shift of the benzylic proton of 4 forms 3. This reaction involves oxidative 3,3,3-trifluoropropylation of an arylaldehyde to afford 4,4,4-trifluoro-1-arylbutan-1-one.
摘要
(E)-三甲基(3,3,3-三氟-1-丙烯基)硅烷（1）与芳醛 2 之间的反应被氟阴离子触发，以中等至良好的收率得到芳基 3,3,3-三氟丙基酮 3。对该反应的机理研究表明，它是通过烯丙基醇盐（4）进行的。随后，4 的苄基质子发生 1,3-质子迁移，形成 3。该反应涉及芳基醛的氧化 3,3,3-三氟丙基化，得到 4,4,4-三氟-1-芳基丁-1-酮。
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