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

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posted on 2021-10-19, 18:08 authored by Shipan Xu, Jun Xie, Yu Liu, Weifeng Xu, Ke-Wen Tang, Biquan Xiong, Wai-Yeung Wong
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.