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

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, 56(5), 1411-1415. doi:10.1002/anie.201609923.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-002C-DBB0-5 Version Permalink: https://hdl.handle.net/21.11116/0000-0008-5395-2
Genre: Journal Article

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Höfler, vGemmeren, Wedemann, Kaupmees, Leito, Leutzsch, Lingnau, List 2017.pdf (Postprint), 545KB
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 Creators:
Höfler, Denis1, Author           
van Gemmeren, Manuel2, Author           
Wedemann, Petra1, Author           
Kaupmees, Karl3, Author
Leito, Ivo3, Author
Leutzsch, Markus1, Author           
Lingnau, Julia B.4, Author           
List, Benjamin1, Author           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Westfälische Wilhelms-Universität Münster, Münster, Germany, ou_persistent22              
3University of Tartu, Institute of Chemistry, Tartu, Estonia, ou_persistent22              
4Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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Free keywords: allylic C-H acids; Brønsted acids; Lewis acids; strong acids; tetratriflylpropene
 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.

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Language(s): eng - English
 Dates: 2016-10-102016-12-222017-01-24
 Publication Status: Issued
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201609923
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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 56 (5) Sequence Number: - Start / End Page: 1411 - 1415 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851