Synthesis of Isothiochroman-3-ones via Metal-Free Oxidative Cyclization of Alkynyl Thioethers

A novel Brønsted acid-catalyzed oxidative C–H functionalization of alkynyl thioethers has been developed. This method allows the practical synthesis of valuable isothiochroman-3-ones in mostly moderate to good yields under mild reaction conditions and features a broad substrate scope and wide functi...

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Bibliographic Details
Published in:Organic letters 2018-12, Vol.20 (23), p.7721-7725
Main Authors: Zhang, Ying-Qi, Zhu, Xin-Qi, Chen, Yang-Bo, Tan, Tong-De, Yang, Ming-Yang, Ye, Long-Wu
Format: Article
Language:English
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Summary:A novel Brønsted acid-catalyzed oxidative C–H functionalization of alkynyl thioethers has been developed. This method allows the practical synthesis of valuable isothiochroman-3-ones in mostly moderate to good yields under mild reaction conditions and features a broad substrate scope and wide functional group tolerance. Moreover, this metal-free oxidation can also be used to promote formal N–H insertion involving an unexpected 1,2-sulfur migration, affording useful 1,4-benzothiazin-3-ones.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03462