A Combined Experimental and Computational Study of NHC-Promoted Desulfonylation of Tosylated Aldimine
A Combined Experimental and Computational Study of NHC-Promoted Desulfonylation of Tosylated Aldimine
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NHC 促进甲苯磺酰化醛亚胺脱磺酰化的实验与计算联合研究
DOI：
10.1039/c9qo01402k
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发表时间：
2020
影响因子：
5.4
通讯作者：
Changsheng Yao
中科院分区：
文献类型：
--
作者：
Fang Sun;Tingrui Yin;Yang Wang;Anni Feng;Liuqing Yang;Wenchao Wu;Chenxia Yu;Tuanjie Li;Donghui Wei;Changsheng Yao
甲苯磺酰化醛亚胺的NHC-催化的双甲酰基化提供了在温和的反应条件下以通常良好至优异的产率和良好的官能团相容性容易地获得芳基腈的途径。DFT计算表明，该反应经历了多个分步过程，包括亲核加成NHC甲苯磺酰亚胺，氮杂-Breslow中间体的形成，去质子化，和甲苯磺酰基基团的解离。
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.