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

Denis Höfler; Manuel van Gemmeren; Petra Wedemann; Karl Kaupmees; Ivo Leito; Markus Leutzsch; Julia B Lingnau; Benjamin List

doi:10.1002/anie.201609923

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

Angew Chem Int Ed Engl. 2017 Jan 24;56(5):1411-1415. doi: 10.1002/anie.201609923. Epub 2016 Dec 22.

Authors

Denis Höfler¹, Manuel van Gemmeren², Petra Wedemann¹, Karl Kaupmees³, Ivo Leito³, Markus Leutzsch¹, Julia B Lingnau¹, Benjamin List¹

Affiliations

¹ Max-Planck Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany.
² Westfälische Wilhelms-Universität Münster, Correnstrasse 40, 48149, Münster, Germany.
³ University of Tartu, Institute of Chemistry, Ravila 14a, Tartu, 50411, Estonia.

PMID: 28004482
DOI: 10.1002/anie.201609923

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.

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

Publication types

Research Support, Non-U.S. Gov't