Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 137-143.DOI: 10.6023/cjoc201808047 Previous Articles     Next Articles

Special Issue: 庆祝陈庆云院士九十华诞

Articles

PhI(OAc)2参与的β-酮酸酯及β-酮酰胺亲核氟化反应

吴文胜, 袁航, 黄高魁, 蒋春辉, 陆鸿飞   

  1. 江苏科技大学环境与化学工程学院 镇江 212003
  • 收稿日期:2018-08-31 修回日期:2018-10-25 出版日期:2019-01-25 发布日期:2018-12-05
  • 通讯作者: 蒋春辉, 陆鸿飞 E-mail:chemjiang@just.edu.cn;zjluhf1979@just.edu.cn
  • 基金资助:

    国家自然科学基金(No.21402067)、江苏省自然科学基金(No.BK20170569)、江苏省高校自然科学基金(No.17KJB150013)资助项目.

Fluorination of β-Ketoesters and β-Ketoamides Based on PhI(OAc)2

Wu Wensheng, Yuan Hang, Huang Gaokui, Jiang Chunhui, Lu Hongfei   

  1. School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003
  • Received:2018-08-31 Revised:2018-10-25 Online:2019-01-25 Published:2018-12-05
  • Contact: 10.6023/cjoc201808047 E-mail:chemjiang@just.edu.cn;zjluhf1979@just.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21402067), the Natural Science Foundation of Jiangsu Province (No. BK20170569) and the Natural Science Fund for Colleges and Universities in Jiangsu Province (No. 17KJB150013).

Herein, a nucleophilic fluorination reaction to construct fluorine-containing β-ketoesters and β-ketoamides is reported. The reaction uses PhI(OAc)2 as oxidant and 3HF·Et3N as fluorinating reagent. It can effectively build a series of fluorochemical compounds containing quaternary carbon center under room temperature reaction conditions for 30 min. Compared with the traditional electrophilic fluorination reaction, this method has the advantages of no metal participation, short reaction time, simple reaction conditions and high reaction yield.

Key words: hypervalent iodine, β-ketoesters, β-ketoamides, nucleophilic fluorination reaction