A mild and practical method for deprotection of aryl methyl/benzyl/allyl ethers with HPPh2 and tBuOK

Wenjing Pan; Chenchen Li; Haoyin Zhu; Fangfang Li; Tao Li; Wanxiang Zhao

doi:10.1039/D1OB01286J

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A mild and practical method for deprotection of aryl methyl/benzyl/allyl ethers with HPPh₂ and ^tBuOK†

Wenjing Pan,^a Chenchen Li,^a Haoyin Zhu,^a Fangfang Li,*^b Tao Li

*^a and Wanxiang Zhao

*^a

Author affiliations

* Corresponding authors

^a State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082, China
E-mail: litao_0922@hnu.edu.cn, zhaowanxiang@hnu.edu.cn

^b The Department of Dermatology, Xiangya Hospital, Central South University, Changsha, Hunan 410008, China
E-mail: xuebingfanger@126.com

Abstract

A general method for the demethylation, debenzylation, and deallylation of aryl ethers using HPPh₂ and ^tBuOK is reported. The reaction features mild and metal-free reaction conditions, broad substrate scope, good functional group compatibility, and high chemical selectivity towards aryl ethers over aliphatic structures. Notably, this approach is competent to selectively deprotect the allyl or benzyl group, making it a general and practical method in organic synthesis.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/D1OB01286J
Article type: Paper
Submitted: 02 Jul 2021
Accepted: 16 Aug 2021
First published: 17 Aug 2021

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Org. Biomol. Chem., 2021,19, 7633-7640

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A mild and practical method for deprotection of aryl methyl/benzyl/allyl ethers with HPPh₂ and ^tBuOK

W. Pan, C. Li, H. Zhu, F. Li, T. Li and W. Zhao, Org. Biomol. Chem., 2021, 19, 7633 DOI: 10.1039/D1OB01286J

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Organic & Biomolecular Chemistry