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1,1,3,3-Tetratriflylpropene (TTP): A Strong, Allylic C–H Acid for Brønsted and Lewis Acid Catalysis

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Höfler,  Denis
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Wedemann,  Petra
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Leutzsch,  Markus
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Lingnau,  Julia
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Höfler, D., van Gemmeren, M., Wedemann, P., Kaupmees, K., Leito, I., Leutzsch, M., et al. (2017). 1,1,3,3-Tetratriflylpropene (TTP): A Strong, Allylic C–H Acid for Brønsted and Lewis Acid Catalysis. Angewandte Chemie International Edition in English, 56(5), 1411-1415. doi:10.1002/anie.201609923.


Cite as: https://hdl.handle.net/11858/00-001M-0000-002C-DBB0-5
Abstract
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.