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N-Alkynylthio Phthalimide: A Shelf-Stable Alkynylthio Transfer Reagent for the Synthesis of Alkynyl Thioethers

Wen-Chao Gao*, Yu-Zhu Shang, Hong-Hong Chang, Xing Li, Wen-Long Wei, Xin-Zhang Yu, Rong Zhou

*Taiyuan University of Technology, Taiyuan 030024, P.R. China, Email: gaowenchaotyut.edu.cn

W.-C. Gao, Y.-Z. Shang, H.-H. Chang, X. Li, W.-L. Wei, X.-Z. Yu, R. Zhou, Org. Lett., 2019, 21, 6021-6024.

DOI: 10.1021/acs.orglett.9b02174 (free Supporting Information)


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Abstract

N-Alkynylthio phthalimides can be easily prepared in three steps from commercially available phthalimide and silver acetylides. N-Alkynylthio phthalimides are efficient electrophilic alkynylthiolating reagents that can react with various C-nucleophiles, including β-ketoesters, aryl boronic acids, and Grignard reagents to afford a diverse range of alkynyl thioethers under mild conditions.

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Key Words

arylation, vinylation, alkynyl sulfides


ID: J54-Y2019