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

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• 作者：Xiaopeng Zhang ; ^{zhangxiaopengv@sina.com} ; Ping Wang ; Xueli Niu ; Zhengwei Li ; Xuesen Fan ; Guisheng Zhang ; ^zgs@htu.cn
• 关键词：Selenium ; Oxidative carbonylation ; 1 ; 4-Dihydro-2H-3 ; 1-benzoxazin-2-one ; 2-Aminobenzyl alcohol ; Phase-transfer catalysis
• 刊名：Chinese Journal of Catalysis
• 出版年：2016
• 出版时间：November 2016
• 年：2016
• 卷：37
• 期：11
• 页码：2034-2038
• 全文大小：600 K
• 卷排序：37

文摘

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 afford 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.