Max-Planck Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany.
Westfälische Wilhelms-Universität Münster, Correnstrasse 40, 48149, Münster, Germany.
Angew Chem Int Ed Engl. 2017 Jan 24;56(5):1411-1415. doi: 10.1002/anie.201609923. Epub 2016 Dec 22.
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.
四三苯基烯(TTP)已被开发为一种高酸性的烯丙基 C-H 酸,可用于 Brønsted 和 Lewis 酸催化。它可以很容易地通过两步法得到,并且在 Mukaiyama 羟醛缩合、Hosomi-Sakurai 和 Friedel-Crafts 酰化反应中始终表现出非凡的催化活性。TTP 及其盐的 X 射线分析证实了其设计的烯丙基结构,其中负电荷分散在四个三氟甲磺酸根上。NMR 实验、酸度测量和理论研究提供了进一步的见解,以合理说明 TTP 的显著反应性。