Issue 29, 2022

Carbocation catalysis in confined space: activation of trityl chloride inside the hexameric resorcinarene capsule

Abstract

Carbocation catalysis can be performed inside the confined space of the hexameric resorcinarene capsule. The inner cavity of the capsule can host the trityl carbocation, which catalyses the Diels–Alder reaction between dienes and unsaturated aldehydes. Experimental results and in silico calculations show that the hexameric resorcinarene capsule C6 can promote the formation of the trityl carbocation from trityl chloride through the cleavage of the carbon–halogen bond promoted by OH⋯X hydrogen bonding. Here it is shown that the combination of the nanoconfined space and the latent carbocation catalysis provides a convenient complementary strategy for the typical carbocation catalysis. The latent strategy bypasses the typical pitfalls associated with active carbocations and provides control of the reaction efficiency in terms of reaction rate, conversion, and selectivity.

Graphical abstract: Carbocation catalysis in confined space: activation of trityl chloride inside the hexameric resorcinarene capsule

Supplementary files

Article information

Article type
Edge Article
Submitted
24 mei 2022
Accepted
06 jun 2022
First published
07 jul 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 8618-8625

Carbocation catalysis in confined space: activation of trityl chloride inside the hexameric resorcinarene capsule

M. De Rosa, S. Gambaro, A. Soriente, P. Della Sala, V. Iuliano, C. Talotta, C. Gaeta, A. Rescifina and P. Neri, Chem. Sci., 2022, 13, 8618 DOI: 10.1039/D2SC02901D

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