A simple protocol for the synthesis of α-substituted phosphonates

Abstract

An efficient, easy-to-handle, and mild substitution reaction approach has been developed for the synthesis of phosphonate derivatives, which are very important in the field of industrial, agricultural, and medicinal chemistry. A large number of nucleophiles, including arylamines, alkylamines, heteroarylamines, primary amines and secondary amines, sulfides, and carbides were attempted to react with α-tosyloxyphosphonate 1. The reaction proceeded under catalyst-free and neat conditions and the corresponding phosphonates 2 were afforded in good yields.

Original language	English
Pages (from-to)	1268-1273
Number of pages	6
Journal	Phosphorus, Sulfur and Silicon and the Related Elements
Volume	191
Issue number	9
DOIs	https://doi.org/10.1080/10426507.2016.1167056
Publication status	Published - 2016

Keywords

catalyst-free
p-toluenesulfonyl chloride
substitution reaction
α-substituted phosphonate

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Inorganic Chemistry

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title = "A simple protocol for the synthesis of α-substituted phosphonates",

abstract = "An efficient, easy-to-handle, and mild substitution reaction approach has been developed for the synthesis of phosphonate derivatives, which are very important in the field of industrial, agricultural, and medicinal chemistry. A large number of nucleophiles, including arylamines, alkylamines, heteroarylamines, primary amines and secondary amines, sulfides, and carbides were attempted to react with α-tosyloxyphosphonate 1. The reaction proceeded under catalyst-free and neat conditions and the corresponding phosphonates 2 were afforded in good yields.",

keywords = "catalyst-free, p-toluenesulfonyl chloride, substitution reaction, α-substituted phosphonate",

author = "Xing Wang and Yuan Cai and Jian Chen and Francis Walter Cornelius Verpoort",

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TY - JOUR

T1 - A simple protocol for the synthesis of α-substituted phosphonates

AU - Wang, Xing

AU - Cai, Yuan

AU - Chen, Jian

AU - Verpoort, Francis Walter Cornelius

PY - 2016

Y1 - 2016

N2 - An efficient, easy-to-handle, and mild substitution reaction approach has been developed for the synthesis of phosphonate derivatives, which are very important in the field of industrial, agricultural, and medicinal chemistry. A large number of nucleophiles, including arylamines, alkylamines, heteroarylamines, primary amines and secondary amines, sulfides, and carbides were attempted to react with α-tosyloxyphosphonate 1. The reaction proceeded under catalyst-free and neat conditions and the corresponding phosphonates 2 were afforded in good yields.

AB - An efficient, easy-to-handle, and mild substitution reaction approach has been developed for the synthesis of phosphonate derivatives, which are very important in the field of industrial, agricultural, and medicinal chemistry. A large number of nucleophiles, including arylamines, alkylamines, heteroarylamines, primary amines and secondary amines, sulfides, and carbides were attempted to react with α-tosyloxyphosphonate 1. The reaction proceeded under catalyst-free and neat conditions and the corresponding phosphonates 2 were afforded in good yields.

KW - catalyst-free

KW - p-toluenesulfonyl chloride

KW - substitution reaction

KW - α-substituted phosphonate

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