PDF herunterladen
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
› InstitutsangabenThis work is supported by Science and Technology Department of Sichuan Province under grant number 2015JY0171.
Weitere Informationen

Publikationsverlauf

Received: 19. März 2017

Accepted after revision: 02. Mai 2017

Publikationsdatum:
20. Juni 2017 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik


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.
  • Supporting Information