External Oxidant‐Free Oxidative Tandem Cyclization: NaI‐Catalyzed Thiolation for the Synthesis of 3‐Thiosubstituted Pyrroles

A simple method for the synthesis of 3‐thiosubstituted pyrroles from homopropargylic amines and thiosulfonates via a tandem sulfenylation/cyclization has been developed. The thiosulfonates are used both as substrates and oxidants in this transformation. This procedure exhibits good functional group...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-11, Vol.361 (22), p.5112-5117
Main Authors: Yuan, Bingxiang, Jiang, Yong, Qi, Zhenjie, Guan, Xin, Wang, Ting, Yan, Rulong
Format: Article
Language:English
Subjects:
3-Thiosubstituted pyrroles
Amines
Chemical synthesis
Functional groups
Homopropargylic amines
Oxidizing agents
Pyrroles
Substrates
Tandem sulfenylation/cyclization
Thiosulfonates
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Summary:A simple method for the synthesis of 3‐thiosubstituted pyrroles from homopropargylic amines and thiosulfonates via a tandem sulfenylation/cyclization has been developed. The thiosulfonates are used both as substrates and oxidants in this transformation. This procedure exhibits good functional group tolerance and a series of 3‐thiosubstituted pyrrole derivatives was obtained in moderate to good yields.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900620