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Issue 11, 2019
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Zinc-catalyzed regioselective C–P coupling of p-quinol ethers with secondary phosphine oxides to afford 2-phosphinylphenols

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Abstract

The zinc triflate-catalyzed highly regioselective C–P cross coupling reaction of p-quinol ethers with secondary phosphine oxides is reported. The reaction provides a facile alternative method for the synthesis of 2-phosphinylphenols in good to high yields. Mechanistically, zinc triflate may serve as an oxophilic σ-Lewis acid to activate the C–O bond in p-quinol ether first. Then the regioselective attack of the phosphorus nucleophile at the α-carbon position takes place to form the C–P bond and give the product. In addition, α-alkynyl substituted p-quinol ethers also react with secondary phosphine oxides in the same reaction mode to give 6-alkynyl 2-phosphinylphenols in the presence of the zinc catalyst.

Graphical abstract: Zinc-catalyzed regioselective C–P coupling of p-quinol ethers with secondary phosphine oxides to afford 2-phosphinylphenols

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Article information


Submitted
17 Jan 2019
Accepted
21 Feb 2019
First published
21 Feb 2019

Org. Biomol. Chem., 2019,17, 2972-2984
Article type
Paper

Zinc-catalyzed regioselective C–P coupling of p-quinol ethers with secondary phosphine oxides to afford 2-phosphinylphenols

M. Zhang, X. Jia, H. Zhu, X. Fang, C. Ji, S. Zhao, L. Han and R. Shen, Org. Biomol. Chem., 2019, 17, 2972
DOI: 10.1039/C9OB00129H

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