A Robust Methodology for the Synthesis of Phosphorothioates, Phosphinothioates and Phosphonothioates,Advanced Synthesis & Catalysis

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A Robust Methodology for the Synthesis of Phosphorothioates, Phosphinothioates and Phosphonothioates
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-03-23 , DOI: 10.1002/adsc.202000059
David J. Jones _{1,

2} , Eileen M. O'Leary ₃ , Timothy P. O'Sullivan _{1,

2,

4}

Affiliation

A robust methodology for the synthesis of phosphorothioates, phosphinothioates and phosphonothioates, including those bearing low molecular weight S‐alkyl side‐chains, is presented. Application of the “caesium effect” in conjunction with the disulfide 3,3’‐dithiobis(propionitrile), which acts as a shelf‐stable sulfur source, avoids recourse to malodorous alkanethiols and toxic P−Cl precursors. A diverse range of sulfur‐containing organophosphorus targets, including phosphorus‐based heterocycles, may be prepared in consistently high yields. This chemistry also provides ready access to the corresponding DBU salts which are potential substrates for Pd‐catalysed coupling reactions.

中文翻译：

合成硫代磷酸酯，硫代磷酸酯和硫代磷酸酯的稳健方法

提出了一种强大的方法来合成硫代磷酸酯，硫代磷酸酯和硫代磷酸酯，包括带有低分子量S-烷基侧链的那些。将“铯效应”与作为货架稳定硫源的二硫化物3,3'-dithiobis（propionitrile）结合使用，可避免使用恶臭的链烷硫醇和有毒的P-Cl前体。可以始终如一的高收率制备各种含硫有机磷靶标，包括基于磷的杂环。这种化学作用还可以方便地获得相应的DBU盐，这些盐是Pd催化偶联反应的潜在底物。

更新日期：2020-03-23

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