Calix[6]arene-based Brønsted acids for molecular recognition and catalysis

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 th...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-02, Vol.19 (7), p.1546-1554
Main Authors: Cera, Gianpiero, Cester Bonati, Federica, Bazzoni, Margherita, Secchi, Andrea, Arduini, Arturo
Format: Article
Language:English
Subjects:
Acidity
Catalysis
Indoles
Ion pairs
Polarity
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Summary: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 (H 2 O, 37 °C). A threading process and catalysis governed by trifluoromethylsulfonamide moieties are reported.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob02393k