Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (10): 2099-2105.DOI: 10.6023/cjoc201403036 Previous Articles     Next Articles

Articles

基于复合氯化剂CuCl2·5/3NaCl·5/2Al2O3的1-氯-2-芳基乙炔的合成

刘淑琴, 赵子剑, 肖竞, 石磊, 冯伶俐, 彭志鸿, 安德烈   

  1. 化学生物传感与计量学国家重点实验室 湖南大学化学化工学院 长沙 410082
  • 收稿日期:2014-03-15 修回日期:2014-05-06 发布日期:2014-06-03
  • 通讯作者: 彭志鸿, 安德烈 E-mail:deliean@hnu.edu.cn
  • 基金资助:

    国家自然科学基金(No. 21072052)和湖南省科技计划(No. 2011 WK4007)资助项目.

Synthesis of 1-Chloro-2-aryl Ethyne Using CuCl2·5/3NaCl·5/2Al2O3 as Composite Chlorinating Agent

Liu Shuqin, Zhao Zijian, Xiao Jing, Shi Lei, Feng Lingli, Peng Zhihong, An Delie   

  1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082
  • Received:2014-03-15 Revised:2014-05-06 Published:2014-06-03
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21072052) and the Hunan Provincial Science and Technology Department Program (No. 2011 WK4007).

An effective protocol for substitution chlorination was accomplished using a new composite chlorinating agent from CuCl2, inorganic salt and carrier. The most appropriate ratio of each individual component of composite chlorinating agent was determined by comparative experiments. The optimal synthetic conditions for 1-chloro-2-aryl ethyne were obtained by the investigation of various factors, including solvents, the amount of composite chlorinating agents and reaction temperature. The mild and simple method allowed the formation of 1-chloro-2-aryl ethyne in up to 99% yields and showed good selectivities. Various substrates bearing inert or sensitive groups were tolerable for the present preparation. A plausible mechanism for the reaction was also proposed.

Key words: composite chlorinating agent, aryl ethyne, substitution chlorination, 1-chloro-2-aryl ethyne