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无催化剂和试剂的 p-醌亚甲基 1,6-膦酰化:一种合成二芳基甲基氧化膦的实用方法。

Catalyst- and reagent-free 1,6-hydrophosphonylation of p-quinone methides: a practical approach for the synthesis of diarylmethyl phosphine oxides.

机构信息

Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.

出版信息

Org Biomol Chem. 2019 Aug 28;17(32):7536-7546. doi: 10.1039/c9ob01326a. Epub 2019 Aug 1.

Abstract

We developed a catalyst-, reagent-, and additive-free protocol with 100% atom economy for the synthesis of diarylmethyl phosphine oxides via 1,6-hydrophosphonylation of p-quinone methides using water as a green solvent. The reaction showed broad scope with excellent functional group tolerance. The practicability of this method was demonstrated by carrying out the reaction on the gram scale whereby product was obtained in high yield by the filtration technique avoiding chromatographic purification.

摘要

我们开发了一种无催化剂、试剂和添加剂的方法,通过水作为绿色溶剂,使 p-醌甲基化物与 1,6-氢膦酰化反应,以 100%原子经济性合成二芳基甲基氧化膦。该反应具有广泛的适用范围和出色的官能团耐受性。通过在克级规模上进行反应,采用过滤技术避免了色谱纯化,以高收率获得产物,证明了该方法的实用性。

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