We describe the application of a novel family of trisulfonamide (TSA) calix[6]arenes in general acid catalysis. Hydrogen-bonding interactions between acidic TSA and methanol boosted the reactivity of the Michael addition of indoles to nitroalkene derivatives. The transformation occurs at a low catalyst loading of 5 mol%, allowing for the synthesis of nitroalkanes with good yields and functional group tolerance.
Trisulfonamide calix[6]arene-catalysed Michael addition to nitroalkenes / Cera, Gianpiero; Balestri, Davide; Bazzoni, Margherita; Marchiò, Luciano; Secchi, Andrea; Arduini, Arturo. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 18:32(2020), pp. 6241-6246. [10.1039/d0ob01319f]
Trisulfonamide calix[6]arene-catalysed Michael addition to nitroalkenes
Cera, Gianpiero
;Balestri, Davide;Bazzoni, Margherita;Marchiò, Luciano;Secchi, Andrea
;Arduini, Arturo
2020-01-01
Abstract
We describe the application of a novel family of trisulfonamide (TSA) calix[6]arenes in general acid catalysis. Hydrogen-bonding interactions between acidic TSA and methanol boosted the reactivity of the Michael addition of indoles to nitroalkene derivatives. The transformation occurs at a low catalyst loading of 5 mol%, allowing for the synthesis of nitroalkanes with good yields and functional group tolerance.| File | Dimensione | Formato | |
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