Selenium-Catalyzed Carbonylation to Phenylcarbamates and Methylene Diphenyl Dicarbamates

doi:10.6023/cjoc201609013

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (2): 411-417.DOI: 10.6023/cjoc201609013 Previous Articles Next Articles

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硒催化羰基化合成苯氨基甲酸酯和二苯甲烷二氨基甲酸酯

张晓鹏, 荆唤芝, 彭惟于, 李亚芳, 范学森, 张贵生

河南师范大学化学化工学院绿色化学介质与反应省部共建教育部重点实验室精细化学品绿色制造河南省协同创新中心新乡 453007

收稿日期:2016-09-12 修回日期:2016-10-12 发布日期:2016-10-18
通讯作者: 张晓鹏, 张贵生 E-mail:zhangxiaopengv@sina.com;zgs@htu.cn
基金资助:
河南省高校科技创新团队支持计划（No.15IRTSTHN003）、河南省高等学校青年骨干教师（No.2013GGJS-059）和河南师范大学青年骨干教师（No.2011-8）资助项目.

Selenium-Catalyzed Carbonylation to Phenylcarbamates and Methylene Diphenyl Dicarbamates

Zhang Xiaopeng, Jing Huanzhi, Peng Weiyu, Li Yafang, Fan Xuesen, Zhang Guisheng

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

Received:2016-09-12 Revised:2016-10-12 Published:2016-10-18
Supported by:
Project supported by the Program for Innovative Research Team in Science and Technology in University of Henan Province (No. 15IRTSTHN003), the Young Backbone Teachers Training Fund of Education Department of Henan Province (No. 2013GGJS-059) and the Young Backbone Teachers Training Fund of Henan Normal University (No. 2011-8).

1. Selenium-Catalyzed Carbonylation to Phenylcarbamates and Methylene Diphenyl Dicarbamates.PDF(510KB)

Abstract

A clean, economical and efficient approach to phenylcarbamates and methylene diphenyl dicarbamates was reported. With cheap and easily available nonmetal selenium as the catalyst, carbon monoxide instead of virulent phosgene as the carbonylation reagent, oxygen as the oxidant, the selenium-catalyzed oxidative carbonylation reaction of aniline could proceed smoothly with alcohols to afford phenylcarbamates mostly in moderate to good yields. Then, catalyzed by HCl/ZnCl₂, the condensation of formaldehyde with the generated phenylcarbamates gave methylene diphenyl dicarbamates in moderate to good yields. The applicability of the substrates was good. Catalyst selenium could be easily recovered due to its function of phase-transfer catalysis and could be recycled. High atomic economy, low cost, no emission of corrosive waste, and phosgene-free condition make this approach very promising. The possible reaction mechanisms were also proposed.

Key words: selenium-catalysis, carbonylation, phenylcarbamate, methylene diphenyl dicarbamate

Cite this article

Zhang Xiaopeng, Jing Huanzhi, Peng Weiyu, Li Yafang, Fan Xuesen, Zhang Guisheng. Selenium-Catalyzed Carbonylation to Phenylcarbamates and Methylene Diphenyl Dicarbamates[J]. Chin. J. Org. Chem., 2017, 37(2): 411-417.

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硒催化羰基化合成苯氨基甲酸酯和二苯甲烷二氨基甲酸酯

Selenium-Catalyzed Carbonylation to Phenylcarbamates and Methylene Diphenyl Dicarbamates

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