Silver-Catalyzed Regioselective Phosphorylation of para-Quinone Methides with P(III)-Nucleophiles

Shipan Xu, Jun Xie, Yu Liu, Weifeng Xu, Ke Wen Tang, Biquan Xiong, Wai Yeung Wong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

Abstract

A simple and efficient method for the silver-catalyzed regioselective phosphorylation of para-quinone methides (p-QMs) with P(III)-nucleophiles (P(OR)3, ArP(OR)2, Ar2P-OR) has been established via Michaelis-Arbuzov-type reaction. A broad range of P(III)-nucleophiles and para-quinone methides are well tolerated under the mild conditions, giving the expected diarylmethyl-substituted organophosphorus compounds with good to excellent yields. Moreover, a series of corresponding enantiomers can be obtained by employing dialkyl arylphosphonite (ArP(OR)2) as substrates. The control experiments and 31P NMR tracking experiments were also performed to gain insights for the plausible reaction mechanism. This protocol may have significant implications for the formation of C(sp3)-P bonds in Michaelis-Arbuzov-type reactions.

Original languageEnglish
Pages (from-to)14983-15003
Number of pages21
JournalJournal of Organic Chemistry
Volume86
Issue number21
DOIs
Publication statusPublished - 5 Nov 2021

ASJC Scopus subject areas

  • Organic Chemistry

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