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Synthesis 2020; 52(02): 208-218
DOI: 10.1055/s-0039-1690749
DOI: 10.1055/s-0039-1690749
feature
Direct Transformation of Propargylic Alcohols and O,O-Diethyl Phosphorothioic Acid into S-(2H-Chromen-4-yl) Phosphorothioates
National Science Foundation of China (No. 21676131 and No. 21462019), the Science Foundation of Jiangxi Province (20181BAB203005 and 20143ACB20012), the Education Department of Jiangxi Province (GJJ180616), Jiangxi Science & Technology Normal University (2017QNBJRC004).Further Information
Publication History
Received: 23 September 2019
Accepted after revision: 31 October 2019
Publication Date:
14 November 2019 (online)
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 - thiophosphatesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690749.
- Supporting Information
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For reviews on the use of propargylic alcohols see: