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A combined experimental and computational study of NHC-promoted desulfonylation of tosylated aldimines

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Abstract

NHC-catalyzed desulfonylation of tosylated aldimines provides facile access to aryl nitriles in generally good to excellent yields with good functional group compatibilities under mild reaction conditions. DFT calculations demonstrate that the reaction undergoes multiple stepwise processes including nucleophilic addition of NHC to tosylated imine, formation of an aza-Breslow intermediate, deprotonation, and dissociation of the tosyl group.

Graphical abstract: A combined experimental and computational study of NHC-promoted desulfonylation of tosylated aldimines

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Article information


Submitted
24 Nov 2019
Accepted
26 Dec 2019
First published
28 Dec 2019

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

A combined experimental and computational study of NHC-promoted desulfonylation of tosylated aldimines

F. Sun, T. Yin, Y. Wang, A. Feng, L. Yang, W. Wu, C. Yu, T. Li, D. Wei and C. Yao, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01402K

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