Transition Metal-Free C-H Thiolation via Sulfonium Salts Using β-Sulfinylesters as the Sulfur Source

Yanhui Chen, Si Wen, Qingyu Tian, Yuqing Zhang and Guolin Cheng*

*College of Materials Science and Engineering, Instrumental Analysis Center, Huaqiao University, Xiamen 361021, China, Email: glchenghqu.edu.cn

Y. Chen, S. Wen, Q. Tian, Y. Zhang, G. Cheng, Org. Lett., 2021, 23, 7905-7909.

DOI: 10.1021/acs.orglett.1c02912

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Abstract

The use of β-sulfinylesters as versatile sulfur source enables direct C(sp)-, C(sp²)-, and C(sp³)-H thiolation reactions. The desired products are formed via chemoselective retro-Michael C-S bond cleavage of sulfonium salts that are formed in situ from the corresponding alkenes, alkynes, and 1,3-dicarboxyl compounds with β-sulfinylesters.

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proposed reaction pathway

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Key Words

vinyl sulfides, akynyl sulfides

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ID: J54-Y2021