Chemical Research in Chinese Universities ›› 2015, Vol. 31 ›› Issue (3): 362-366.doi: 10.1007/s40242-015-4456-0

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Difluoromethylation of 2-Hydroxychalcones Using Sodium 2-Chloro-2,2-difluoroacetate as Difluoromethylating Agent

WANG Wei1, HUA Mingqing1, HUANG Yan1, ZHANG Qi1,2, ZHANG Xiaoyan1, WU Jingbo1   

  1. 1. School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, P. R. China;
    2. Hainan Provincial Key Laboratory of Fine Chemistry, Hainan University, Haikou 570228, P. R. China
  • Received:2014-12-01 Revised:2015-03-17 Online:2015-06-01 Published:2015-03-16
  • Contact: HUA Mingqing, ZHANG Qi E-mail:huamq840710@163.com;qzhang@ujs.edu.cn
  • Supported by:

    Supported by the National Natural Science Foundation of China(Nos.21302071, 21261008, 21204031), the Natural Science Foundation of Jiangsu Province, China(No.BK20130484), the Scientific Research Foundation for Advanced Talents of Jiangsu University, China(No.12JDG089/14JDG054) and the Hainan International Science and Technology Cooperation, China (No.KJHZ2014-05).

Abstract:

Difluoromethylation of 2-hydroxychalcones using sodium 2-chloro-2,2-difluoroacetate as the difluoro-methylating agent was developed. Under facile conditions, a wide range of aryl difluoromethyl ethers were obtained in yields of 36%-80%. It is noteworthy that the new addition products, 2,2-difluoro-2H-benzofuran derivatives, were also synthesized in the reactions. The yield of 2,2-difluoro-2H-benzofuran derivative could be up to 35% when 3-methyl-2-hydroxychalcone was used as the reactant. A plausible reaction mechanism was proposed.

Key words: Difluoromethylation, 2-Hydroxychalcone, 2-Difluoromethoxychalcone, 2,2-Difluoro-2H-benzofuran