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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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
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spelling sg-ntu-dr.10356-1703202024-05-17T15:31:45Z Carbene-catalyzed access to thiochromene derivatives: control of reaction pathways via slow release of thiols from disulfides Wu, Qifei Wu, Shuquan Zou, Juan Wang, Qingyun Mou, Chengli Zheng, Pengcheng Chi, Robin Yonggui School of Chemistry, Chemical Engineering and Biotechnology Chemistry Heterocyclic Compounds Carbenes 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. Ministry of Education (MOE) Nanyang Technological University National Research Foundation (NRF) Submitted/Accepted version We acknowledge funding supports from the National Natural Science Foundation of China (21732002, 22061007 and 22071036); Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [Qianjiaohe KY number (2020)004]; The 10 Talent Plan (Shicengci) of Guizhou Province ([2016] 5649); Science and Technology Department of Guizhou Province [Qiankehe-jichu-ZK[2022]zhongdian024], ([2018]2802, [2019]1020); Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023) at Guizhou University; Singapore National Research Foundation under its NRF Investigatorship (NRF-NRFI2016-06) and Competitive Research Program (NRF-CRP22-2019-0002); Ministry of Education, Singapore, under its MOE AcRF Tier 1 Award (RG7/20, RG70/21), MOE AcRF Tier 2 (MOE2019-T2-2-117), and MOE AcRF Tier 3 Award (MOE2018-T3-1-003); a Chair Professorship Grant, and Nanyang Technological University. 2023-09-07T01:46:19Z 2023-09-07T01:46:19Z 2023 Journal Article Wu, Q., Wu, S., Zou, J., Wang, Q., Mou, C., Zheng, P. & Chi, R. Y. (2023). Carbene-catalyzed access to thiochromene derivatives: control of reaction pathways via slow release of thiols from disulfides. Organic Letters, 25(21), 3967-3971. https://dx.doi.org/10.1021/acs.orglett.3c01414 1523-7060 https://hdl.handle.net/10356/170320 10.1021/acs.orglett.3c01414 37200161 2-s2.0-85160805962 21 25 3967 3971 en NRF-NRFI2016-06 NRF-CRP22-2019-0002 RG7/20 RG70/21 MOE2019-T2-2-117 MOE2018-T3-1-003 Organic Letters © 2023 American Chemical Society. All rights reserved. This article may be downloaded for personal use only. Any other use requires prior permission of the copyright holder. The Version of Record is available online at http://doi.org/10.1021/acs.orglett.3c01414. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Chemistry
Heterocyclic Compounds
Carbenes
spellingShingle Chemistry
Heterocyclic Compounds
Carbenes
Wu, Qifei
Wu, Shuquan
Zou, Juan
Wang, Qingyun
Mou, Chengli
Zheng, Pengcheng
Chi, Robin Yonggui
Carbene-catalyzed access to thiochromene derivatives: control of reaction pathways via slow release of thiols from disulfides
description 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.
author2 School of Chemistry, Chemical Engineering and Biotechnology
author_facet School of Chemistry, Chemical Engineering and Biotechnology
Wu, Qifei
Wu, Shuquan
Zou, Juan
Wang, Qingyun
Mou, Chengli
Zheng, Pengcheng
Chi, Robin Yonggui
format Article
author Wu, Qifei
Wu, Shuquan
Zou, Juan
Wang, Qingyun
Mou, Chengli
Zheng, Pengcheng
Chi, Robin Yonggui
author_sort Wu, Qifei
title Carbene-catalyzed access to thiochromene derivatives: control of reaction pathways via slow release of thiols from disulfides
title_short Carbene-catalyzed access to thiochromene derivatives: control of reaction pathways via slow release of thiols from disulfides
title_full Carbene-catalyzed access to thiochromene derivatives: control of reaction pathways via slow release of thiols from disulfides
title_fullStr Carbene-catalyzed access to thiochromene derivatives: control of reaction pathways via slow release of thiols from disulfides
title_full_unstemmed Carbene-catalyzed access to thiochromene derivatives: control of reaction pathways via slow release of thiols from disulfides
title_sort carbene-catalyzed access to thiochromene derivatives: control of reaction pathways via slow release of thiols from disulfides
publishDate 2023
url https://hdl.handle.net/10356/170320
_version_ 1806059797359886336

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