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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Visible light-induced cascade cyclization of 2-isocyanoaryl thioethers/selenoethers: access to
Dan Liu1, Shichao Yang1, Huanfeng Jiang1
1Key Laboratory of Functional Molecular Engineering of Guangdong Province, State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China. cewuwq@scut.edu.cn.
Abstract:
Herein, we describe an efficient and atom-economical strategy for the synthesis of 2-arylthiobenzothiazole and 2-arylthiobenzoselenazole compounds via visible light-induced cascade cyclization of 2-isocyanoaryl thioethers/selenoethers with diaryl disulfides. Among them, two C-X (X = S, Se) bonds were formed under mild conditions in one single operation through thiyl radical addition to the isocyano groups of 2-isocyanoaryl thioethers/selenoethers followed by an annulation process. This protocol features excellent chemical selectivity, good functional group tolerance, simple operation and mild reaction conditions. Moreover, the derivatization reaction of the newly formed 2-arylthiobenzothiazole products demonstrates the utility of this method in organic synthesis.
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Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.