Selenium-catalyzed oxidative carbonylation of 2-aminobenzyl alcohol to give 1,4-dihydro-2H-3,1-benzoxazin-2-one

doi:10.1016/S1872-2067(16)62537-8

Chinese Journal of Catalysis ›› 2016, Vol. 37 ›› Issue (11): 2034-2038.DOI: 10.1016/S1872-2067(16)62537-8

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Selenium-catalyzed oxidative carbonylation of 2-aminobenzyl alcohol to give 1,4-dihydro-2H-3,1-benzoxazin-2-one

Xiaopeng Zhang, Ping Wang, Xueli Niu, Zhengwei Li, Xuesen Fan, Guisheng Zhang

Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, Henan, China

Received:2016-07-05 Revised:2016-08-09 Online:2016-11-25 Published:2016-11-25
Contact: Xiaopeng Zhang,Tel:+86-373-3326335; Fax:+86-373-3325250; E-mail:zhangxiaopengv@sina.com;Guisheng Zhang,Tel/Fax:+86-373-3325250; E-mail:zgs@htu.cn
Supported by:
This work was supported by the Program for Changjiang Scholars and Innovative Research Team in University (IRT1061), the Program for Innova-tive Research Team in Science and Technology in University of Henan Province (15IRTSTHN003), the Young Backbone Teachers Training Fund of the Education Department of Henan Province (2013GGJS-059), and Henan Normal University (2011-8).

Abstract

Abstract:

An efficient, economical, and phosgene-free approach was developed for the preparation of 1,4-dihydro-2H-3,1-benzoxazin-2-one from 2-aminobenzyl alcohol. In terms of its key features, this reaction uses the cheap and recyclable non-metal selenium as a catalyst instead of the noble metal palladium; carbon monoxide as a carbonylation agent instead of virulent phosgene or one of its derivatives; and oxygen as an oxidant. The selenium-catalyzed oxidative carbonylation reaction of 2-aminobenzyl alcohol proceeded efficiently in a single pot in the presence of triethylamine to af-ford 1,4-dihydro-2H-3,1-benzoxazin-2-one in 87% yield. Furthermore, the selenium catalyst was readily recovered and recycled, affording a product yield of 80% after five cycles.

Key words: Selenium, Oxidative carbonylation, 1, 4-Dihydro-2H-3, 1-benzoxazin-2-one 2-Aminobenzyl alcohol, Phase-transfer catalysis

Xiaopeng Zhang, Ping Wang, Xueli Niu, Zhengwei Li, Xuesen Fan, Guisheng Zhang. Selenium-catalyzed oxidative carbonylation of 2-aminobenzyl alcohol to give 1,4-dihydro-2H-3,1-benzoxazin-2-one[J]. Chinese Journal of Catalysis, 2016, 37(11): 2034-2038.

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Selenium-catalyzed oxidative carbonylation of 2-aminobenzyl alcohol to give 1,4-dihydro-2H-3,1-benzoxazin-2-one

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