Direct reaction of nitroarenes and thiols via photodriven oxygen atom transfer for access to sulfonamides
Sulfonamide is a common motif in medicines and agrochemicals. Typically, this class of functional groups is prepared by reacting amines with sulfonyl chlorides that are presynthesized from nitro compounds and thiols, respectively. Here, we report a novel strategy that directly couples nitro compound...
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sg-ntu-dr.10356-1647552023-04-21T15:31:47Z Direct reaction of nitroarenes and thiols via photodriven oxygen atom transfer for access to sulfonamides Bao, Zhaowei Zou, Juan Mou, Chengli Jin, Zhichao Ren, Shi-Chao Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry Thiol Derivative Nitro Compounds Sulfonamide is a common motif in medicines and agrochemicals. Typically, this class of functional groups is prepared by reacting amines with sulfonyl chlorides that are presynthesized from nitro compounds and thiols, respectively. Here, we report a novel strategy that directly couples nitro compounds and thiols to form sulfonamides atom- and redox-economically. Mechanistic studies suggest our reaction proceeds via direct photoexcitation of nitroarenes that eventually transfers the oxygen atoms from the nitro group to the thiol unit. Ministry of Education (MOE) Nanyang Technological University National Research Foundation (NRF) Submitted/Accepted version We acknowledge financial support from the National Natural Science Foundation of China (21961006, 32172459, 22071036), The 10 Talent Plan (Shicengci) of Guizhou Province ([2016]5649), the Science and Technology Department of Guizhou Province ([2019]1020, QiankehejichuZK[2021]Key033), the Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023) at Guizhou University, Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [Qianjiaohe KY (2020)004], the Guizhou Province First-Class Disciplines Project [(Yiliu Xueke Jianshe Xiangmu)-GNYL(2017)008], Guizhou University of Traditional Chinese Medicine, and Guizhou University (China), Singapore National Research Foundation under its NRF Investigatorship (NRF-NRFI2016-06) and Competitive Research Program (NRF-CRP22-2019-0002), the Ministry of Education, Singapore, under its MOE AcRF Tier 1 Award (RG7/20, RG5/19), MOE AcRF Tier 2 (MOE2019-T2-2- 117), MOE AcRF Tier 3 Award (MOE2018-T3-1-003), and Nanyang Research Award Grant, Chair Professorship Grant, Nanyang Technological University. 2023-02-13T07:15:38Z 2023-02-13T07:15:38Z 2022 Journal Article Bao, Z., Zou, J., Mou, C., Jin, Z., Ren, S. & Chi, R. Y. (2022). Direct reaction of nitroarenes and thiols via photodriven oxygen atom transfer for access to sulfonamides. Organic Letters, 24(48), 8907-8913. https://dx.doi.org/10.1021/acs.orglett.2c03770 1523-7060 https://hdl.handle.net/10356/164755 10.1021/acs.orglett.2c03770 36421405 2-s2.0-85143066648 48 24 8907 8913 en NRF-NRFI2016-06 NRF-CRP22-2019-0002 RG7/20 RG5/19 MOE2019-T2-2-117 MOE2018-T3-1-003 Organic Letters This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © 2022 American Chemical Society, after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org//10.1021/acs.orglett.2c03770. application/pdf |
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Science::Chemistry Thiol Derivative Nitro Compounds Bao, Zhaowei Zou, Juan Mou, Chengli Jin, Zhichao Ren, Shi-Chao Chi, Robin Yonggui Direct reaction of nitroarenes and thiols via photodriven oxygen atom transfer for access to sulfonamides |
| description |
Sulfonamide is a common motif in medicines and agrochemicals. Typically, this class of functional groups is prepared by reacting amines with sulfonyl chlorides that are presynthesized from nitro compounds and thiols, respectively. Here, we report a novel strategy that directly couples nitro compounds and thiols to form sulfonamides atom- and redox-economically. Mechanistic studies suggest our reaction proceeds via direct photoexcitation of nitroarenes that eventually transfers the oxygen atoms from the nitro group to the thiol unit. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Bao, Zhaowei Zou, Juan Mou, Chengli Jin, Zhichao Ren, Shi-Chao Chi, Robin Yonggui |
| format |
Article |
| author |
Bao, Zhaowei Zou, Juan Mou, Chengli Jin, Zhichao Ren, Shi-Chao Chi, Robin Yonggui |
| author_sort |
Bao, Zhaowei |
| title |
Direct reaction of nitroarenes and thiols via photodriven oxygen atom transfer for access to sulfonamides |
| title_short |
Direct reaction of nitroarenes and thiols via photodriven oxygen atom transfer for access to sulfonamides |
| title_full |
Direct reaction of nitroarenes and thiols via photodriven oxygen atom transfer for access to sulfonamides |
| title_fullStr |
Direct reaction of nitroarenes and thiols via photodriven oxygen atom transfer for access to sulfonamides |
| title_full_unstemmed |
Direct reaction of nitroarenes and thiols via photodriven oxygen atom transfer for access to sulfonamides |
| title_sort |
direct reaction of nitroarenes and thiols via photodriven oxygen atom transfer for access to sulfonamides |
| publishDate |
2023 |
| url |
https://hdl.handle.net/10356/164755 |
| _version_ |
1764208005499322368 |