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1,1,3,3‐Tetratriflylpropene (TTP): A Strong, Allylic C–H Acid for Brønsted and Lewis Acid Catalysis
Author(s) -
Höfler Denis,
van Gemmeren Manuel,
Wedemann Petra,
Kaupmees Karl,
Leito Ivo,
Leutzsch Markus,
Lingnau Julia B.,
List Benjamin
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201609923
Subject(s) - allylic rearrangement , chemistry , lewis acids and bases , catalysis , reactivity (psychology) , brønsted–lowry acid–base theory , delocalized electron , aldol reaction , lewis acid catalysis , medicinal chemistry , acid catalysis , acylation , organic chemistry , medicine , alternative medicine , pathology
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.