TBHP-mediated photochemical coupling/cyclization of -arylacrylamides with thiols

The effective photoredox-mediated oxidative thiolation and cyclization of N -arylacrylamides with thiols leads to biologically interesting 3-thionated oxindoles through C-S and C-C bond formation. This process represents a straightforward reaction that starts from non-prefunctionalized thiolating re...

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Veröffentlicht in:Organic & biomolecular chemistry 2023-02, Vol.21 (5), p.94-944
Hauptverfasser: Qu, Zhonghua, Ji, Xiaochen, Tian, Lin, Mao, Guojiang, Deng, Guo-Jun, Huang, Huawen
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container_issue 5
container_start_page 94
container_title Organic & biomolecular chemistry
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creator Qu, Zhonghua
Ji, Xiaochen
Tian, Lin
Mao, Guojiang
Deng, Guo-Jun
Huang, Huawen
description The effective photoredox-mediated oxidative thiolation and cyclization of N -arylacrylamides with thiols leads to biologically interesting 3-thionated oxindoles through C-S and C-C bond formation. This process represents a straightforward reaction that starts from non-prefunctionalized thiolating reagents. Mechanistic studies demonstrated that the TBHP serves as a key radical initiator with visible-light catalysis. TBHP-mediated thiyl couplings: A mild and metal-free visible-light-induced system allows sequential thiolation/cyclization of N -aryl acrylamides and mercaptans and provides an access to thionated oxindoles with potential biological activity.
doi_str_mv 10.1039/d2ob02187k
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title TBHP-mediated photochemical coupling/cyclization of -arylacrylamides with thiols
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