Direct Transformation of Propargylic Alcohols and O,O-Diethyl Phosphorothioic Acid into S-(2H-Chromen-4-yl) Phosphorothioates

Xian-Rong Song; Tao Yang; Haixin Ding; Qiang Xiao

doi:10.1055/s-0039-1690749

Synthesis, Table of Contents

Synthesis 2020; 52(02): 208-218
DOI: 10.1055/s-0039-1690749

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Direct Transformation of Propargylic Alcohols and O,O-Diethyl Phosphorothioic Acid into S-(2H-Chromen-4-yl) Phosphorothioates

Xian-Rong Song

,

Tao Yang

,

Haixin Ding

,

Qiang Xiao ∗

Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Jiangxi Province, Nanchang 330013, P. R. of China Email: xiaoqiang@tsinghua.org.cn

› Author Affiliations

Abstract

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Abstract

An environmentally benign and efficient method has been successfully developed to generate S-(2H-chromen-4-yl) phosphorothioates from easily available 2-(3-hydroxyprop-1-ynyl)phenols and O,O-diethyl phosphorothioic acid [(EtO)₂P(O)SH] with water as the only byproduct. The reaction proceeds smoothly in moderate to excellent yields. It is noted that (EtO)₂P(O)SH acts not only as an acid promoter, but also as the nucleophile to attack the allenic carbocation intermediate.

Key words

propargylic alcohols - phosphorothioic acids - phosphorothioates - cascade cyclization - thiophosphates

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References

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