Cu-Catalyzed Diarylthiolation of Ynones with Aryl Iodides and Elemental Sulfur: An Access to Tetrasubstituted (Z)‑1,2-Bis(arylthio)alkenes and Benzo[b][1,4]dithiines

A copper-catalyzed three-component reaction of ynones, aryl iodides, and elemental sulfur via a syn-addition process is established. The reaction features operational practicality, broad substrate scope, and readily accessible scale-up synthesis by affording a series of (Z)-1,2-bis­(arylthio)­alkene...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-09, Vol.87 (17), p.11796-11804
Main Authors: Zhao, Yi-Ming, Wang, Xu, Guo, Zi-Yi, Li, Hang, Zhang, Ji-Tan, Xie, Mei-Hua
Format: Article
Language:English
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Summary:A copper-catalyzed three-component reaction of ynones, aryl iodides, and elemental sulfur via a syn-addition process is established. The reaction features operational practicality, broad substrate scope, and readily accessible scale-up synthesis by affording a series of (Z)-1,2-bis­(arylthio)­alkenes in good to excellent yield. Moreover, benzo­[b]­[1,4]­dithiines can be also constructed efficiently by using 1,2-diiodobenzene as the coupling partner.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01575