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Synthesis 2017; 49(17): 4017-4024
DOI: 10.1055/s-0036-1589035
paper
© Georg Thieme Verlag Stuttgart · New York

Tetrabutylammonium Iodide Catalyzed Epoxidation of Naphthoquinone Derivatives with tert-Butyl Hydroperoxide as an Oxidant

Bai-Ru Ai
a   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China   Email: Jiyuwang@cioc.ac.cn
b   University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Xu-Ling Chen
a   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China   Email: Jiyuwang@cioc.ac.cn
b   University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Yu Dong
a   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China   Email: Jiyuwang@cioc.ac.cn
b   University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Lei Tang*
c   Laboratory of Anaestheisa & Critical Care Medicine, Translational Neuroscience Center, and Department of Anaesthesiology, West China Hospital, Sichuan University, Chengdu 610041, P. R. of China   Email: manstein_1984@sina.com
,
Ji-Yu Wang*
a   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China   Email: Jiyuwang@cioc.ac.cn
› Author AffiliationsThis work is supported by Science and Technology Department of Sichuan Province under grant number 2015JY0171.
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Publication History

Received: 19 March 2017

Accepted after revision: 02 May 2017

Publication Date:
20 June 2017 (online)

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Abstract

An efficient and environmentally benign procedure has been developed for the epoxidation of naphthoquinone derivatives by using tetrabutylammonium iodide as a catalyst and tert-butyl hydroperoxide as an oxidant in the presence of silicon dioxide. This protocol, which provides a facile base-free methodology for the synthesis of some new naphthoquinone-based epoxides, features mild reaction conditions, high yields, remarkably short reaction time, and broad substrate scope

Key words

naphthoquinone derivates - expoxidation - tetrabutyl­ammonium iodide - tert-butyl hydroperoxide - silicon dioxide

Supporting Information

    Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589035.
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