1,1,3,3-Tetratriflylpropene (TTP): A Strong, Allylic C-H Acid for Brønsted and Lewis Acid Catalysis
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- 作者：Denis Hö ; fler ; Dr. Manuel van Gemmeren ; Petra Wedemann ; Dr. Karl Kaupmees ; Prof. Dr. Ivo Leito ; Dr. Markus Leutzsch ; Julia B. Lingnau and Prof. Dr. Benjamin List
- 刊名：Angewandte Chemie International Edition
- 出版年：2017
- 出版时间：January 24, 2017
- 年：2017
- 卷：56
- 期：5
- 页码：1411-1415
- 全文大小：2181K
- ISSN：1521-3773
文摘
Tetratrifylpropene (TTP) has been developed as a highly acidic, allylic C–H acid for Brønsted and Lewis acid catalysis. It can readily be obtained in two steps and consistently shows exceptional catalytic activities for Mukaiyama aldol, Hosomi–Sakurai, and Friedel–Crafts acylation reactions. X-ray analyses of TTP and its salts confirm its designed, allylic structure, in which the negative charge is delocalized over four triflyl groups. NMR experiments, acidity measurements, and theoretical investigations provide further insights to rationalize the remarkable reactivity of TTP.