A combined experimental and computational study of NHC-promoted desulfonylation of tosylated aldimines
Literature Information
Publication Date
2019-12-28
DOI
10.1039/C9QO01402K
Impact Factor
5.281
Authors
Fang Sun, Tingrui Yin, Yang Wang, Anni Feng, Liuqing Yang, Wenchao Wu, Chenxia Yu, Tuanjie Li, Donghui Wei, Changsheng Yao
View Original
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.
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Organic Chemistry Frontiers
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