Metal-free α-alkylation of alcohols with para-quinone methides

Jifeng Qi; Ziyang Deng; Bo Huang; Sunliang Cui

doi:10.1039/C8OB00568K

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Metal-free α-alkylation of alcohols with para-quinone methides†

Jifeng Qi,^a Ziyang Deng,^a Bo Huang^a and Sunliang Cui

*^ab

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* Corresponding authors

^a Institute of Drug Discovery and Design, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P. R. China
E-mail: slcui@zju.edu.cn

^b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

Abstract

A metal-free α-alkylation of alcohols with para-quinone methides (p-QMs) for accessing alcohol-containing phenols and dihydroisocoumarins has been developed. The alcohols were converted to α-oxy radicals in the presence of di-tert-butyl peroxide (DTBP), which were added to p-QMs for aromatization and C(sp³)–C(sp³) bond formation.

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

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DOI: https://doi.org/10.1039/C8OB00568K
Article type: Paper
Submitted: 07 Mar 2018
Accepted: 14 Mar 2018
First published: 16 Mar 2018

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Org. Biomol. Chem., 2018,16, 2762-2767

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Metal-free α-alkylation of alcohols with para-quinone methides

J. Qi, Z. Deng, B. Huang and S. Cui, Org. Biomol. Chem., 2018, 16, 2762 DOI: 10.1039/C8OB00568K

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Organic & Biomolecular Chemistry

Metal-free α-alkylation of alcohols with para-quinone methides†

Abstract

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Metal-free α-alkylation of alcohols with para-quinone methides

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