Selectivity Controlled Hydroamination of Alkynes to Sulfonyl Fluoride Hubs: Development and Application

Xueying Bai, Liliang Huang*, Pengyu Zhou, Hui Xi, Junduo Hu, Zhicheng Zuo and Huangdi Feng*

*College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620, China, Email: llhuangsues.edu.cn, hdfengsues.edu.cn

X. Bai, L. Huang, P. Zhou, H. Xi, J. Hu, Z. Zuo, H. Feng, J. Org. Chem., 2022, 87, 4998-5004.

DOI: 10.1021/acs.joc.1c03082

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Abstract

A hydroamination of unactivated alkynes with lithium bis(fluorosulfonyl)imide (LiN(SO₂F)₂) provides a single regioisomer of a sulfonyl fluoride in very good yields under mild conditions. This method offers broad functional group compatibility and delivers the target vinyl fluorosulfonimides even in gram-scale. Vinyl fluorosulfonimides can be used for the synthesis of fluorosulfates and diphenyl sulfate.

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Key Words

enamines

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ID: J42-Y2022