(E)-Trimethyl(perfluoroprop-1-enyl)silane As a Reagent to Transfer Perfluoroprop-1-enyl Group to Ketones and Aldehydes Catalyzed by Fluoride

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• 作者：Roman B. Larichev ; Viacheslav A. Petrov ; Gerard J. Grier ; Mario J. Nappa ; William J. Marshall ; Alexander A. Marchione ; Rebecca J. Dooley
• 刊名：Organic Process Research & Development
• 出版年：2014
• 出版时间：August 15, 2014
• 年：2014
• 卷：18
• 期：8
• 页码：1060-1066
• 全文大小：329K
• ISSN：1520-586X

文摘

Analogous to trifluoromethyltrimethylsilane (Ruppert鈥檚 reagent) (E)-trimethyl(perfluoroprop-1-enyl)silane (1), prepared by deprotonation of (Z)-1,2,3,3,3-pentafluoroprop-1-ene (2a) at 鈭?8 掳C in the presence of chlorotrimethylsilane, was shown to transfer the perfluoroprop-1-enyl group to a number of electrophiles containing carbonyl group in the presence of catalytic amount of fluoride anion. The perfluoroprop-1-enyl group was transferred to formaldehyde, acetaldehyde, benzaldehyde, acetone, trifluoroacetophenone resulting in formation of corresponding TMS-ethers of secondary and tertiary alcohols containing Z-CF₃CF鈺怌F鈥?fragment. With some substrates such as hexafluoroacetone, formaldehyde, and trifluoroacetophenone, substituted 5-membered dioxolane products of the reaction can be obtained, depending on the reaction conditions and the source of fluoride catalyst.