Cera Gianpiero, Cester Bonati Federica, Bazzoni Margherita, Secchi Andrea, Arduini Arturo
Università di Parma, Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, Parco Area delle Scienze 17/A, 43124 Parma, Italy.
Org Biomol Chem. 2021 Feb 25;19(7):1546-1554. doi: 10.1039/d0ob02393k.
We report the synthesis of a versatile trifluoromethylsulfonamide calix[6]arene derivative with Brønsted acid features which can influence both molecular recognition and catalytic application. Indeed, in low polarity media, the trifluoromethyl-containing supramolecular wheel is able to respond to the complexation with charged species as a function of its selective ion-pair recognition. In parallel, the enhanced acidity is the key to promote Michael additions of indoles to nitroalkenes under pseudo-physiological reaction conditions (H2O, 37 °C).
我们报道了一种具有布朗斯特酸特性的多功能三氟甲基磺酰胺杯[6]芳烃衍生物的合成，该衍生物可同时影响分子识别和催化应用。实际上，在低极性介质中，含三氟甲基的超分子轮能够根据其选择性离子对识别作用，对与带电物种的络合做出响应。同时，增强的酸度是在伪生理反应条件（水，37℃）下促进吲哚与硝基烯烃发生迈克尔加成反应的关键。
