Carbene-catalyzed access to thiochromene derivatives: control of reaction pathways via slow release of thiols from disulfides

Carbene-catalyzed access to thiochromene derivatives: control of reaction pathways via slow release of thiols from disulfides

Substrates containing disulfide bonds, which are more stable and less smelling, could be used as thiophenol precursors in organic synthesis. Herein, an N-heterocyclic carbene (NHC)-catalyzed reaction between α-bromoenals and 2,2'-dithiodibenzaldehydes was developed. Through the sustained releas...

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Bibliographic Details
Main Authors: Wu, Qifei, Wu, Shuquan, Zou, Juan, Wang, Qingyun, Mou, Chengli, Zheng, Pengcheng, Chi, Robin Yonggui
Other Authors: School of Chemistry, Chemical Engineering and Biotechnology
Format: Article
Language:English
Published: 2023
Subjects:
Chemistry
Heterocyclic Compounds
Carbenes
Online Access:https://hdl.handle.net/10356/170320
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Institution: Nanyang Technological University
Language: English
Description
Summary:Substrates containing disulfide bonds, which are more stable and less smelling, could be used as thiophenol precursors in organic synthesis. Herein, an N-heterocyclic carbene (NHC)-catalyzed reaction between α-bromoenals and 2,2'-dithiodibenzaldehydes was developed. Through the sustained release strategy, the side reaction can be effectively inhibited, and the chiral thiochromene derivatives can be obtained with good yields and high optical purities. Application studies showed encouraging results when the desired products were explored for antimicrobial utilities in pesticide development.

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