有机化学 ›› 2016, Vol. 36 ›› Issue (5): 1034-1043.DOI: 10.6023/cjoc201512018 上一篇    下一篇

研究论文

铜-银双金属纳米颗粒催化的醛-端炔加成反应研究

王超, 邓楠, 王玲玲, 许定健, 姚小泉   

  1. 南京航空航天大学材料科学与技术学院 南京 210016
  • 收稿日期:2015-12-13 修回日期:2016-01-15 发布日期:2016-02-01
  • 通讯作者: 姚小泉 E-mail:yaoxq@nuaa.edu.cn
  • 基金资助:

    国家自然科学基金(No.21172107)、江苏高校优势学科建设工程资助项目.

Cu-Ag Bimetallic Nanoparticles Catalyzed Addition of Terminal Alkynes to Aldehydes

Wang Chao, Deng Nan, Wang Lingling, Xu Dingjian, Yao Xiaoquan   

  1. Department of Applied Chemistry, Nanjing University of Aeronautics and Astronautics, Nanjing 210016
  • Received:2015-12-13 Revised:2016-01-15 Published:2016-02-01
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21172107), and the Priority Academic Program Development of Jiangsu Higher Education Institutions.

采用铜-银双金属纳米颗粒作为催化剂,在2,2'-联吡啶作为配体的修饰作用下,发展了一个高效的、双金属催化的醛-端炔加成生成炔丙醇化合物的反应体系.在该催化体系中,铜-银双金属纳米颗粒催化剂表现出独特的双金属协同效应,银纳米颗粒作为助催化剂有效提高了铜催化剂的催化效能.与文献相比,该反应条件温和、底物适应性优良,且无需溶剂.该反应中,催化剂可以实现有效循环利用,并可有效放大到克级规模反应.

关键词: 铜银双金属纳米颗粒, 共催化, 醛-炔加成, 炔丙醇, 协同效应

A copper-silver nanoparticles-catalyzed addition of terminal alkynes to aldehydes was developed for the synthesis of propargyl alcohols. With the promotion of bipyridine ligand, the bimetallic catalyst showed highly efficient to the reaction under neat condition, and good to excellent yields were achieved for various propargylic alcohols. In this catalytic reaction, a remarkable bimetallic synergistic effect was observed, in which Ag NPs worked as the co-catalyst and improved the catalytic activity of Cu NPs significantly. The nanoparticle catalyst could be recovered and reused effectively, and no obvious reduction on catalytic activity was observed after four recycles. Furthermore, a gram-scale reaction was also carried out successfully.

Key words: Cu-Ag bimetallic nanoparticles, co-catalysis, the addition of terminal alkynes to aldehydes, propargylic alcohols, synergistic effect