有机化学 ›› 2015, Vol. 35 ›› Issue (10): 2095-2101.DOI: 10.6023/cjoc201505025 上一篇    下一篇

研究论文

银催化炔丙醇与芳基异腈交叉偶联反应:原子经济性合成N-芳基-2,3-联烯酰胺

徐文帅a, 赵寿经a, 骆晓沛a, 宋金娜a, 刘建全b, 毕锡和b, 廖沛球b   

  1. a 吉林大学生物与农业工程学院 长春 130022;
    b 东北师范大学化学学院 长春 130024
  • 收稿日期:2015-05-19 修回日期:2015-06-15 发布日期:2015-06-24
  • 通讯作者: 宋金娜, 廖沛球 E-mail:songjn2010@jlu.edu.cn;liaopq774@nenu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. 31101010, 21202016和21372038)资助项目.

Silver-Catalyzed Cross-Coupling Reaction of Propargylic Alcohols and Arylisocyanides: An Atom-Economic Synthesis of N-Aryl-2,3-allenamides

Xu Wenshuaia, Zhao Shoujinga, Luo Xiaopeia, Song Jinnaa, Liu Jianquanb, Bi Xiheb, Liao Peiqiub   

  1. a College of Biological and Agricultural Engineering, Jilin University, Changchun 130022;
    b Department of Chemistry, Northeast Normal University, Changchun 130024
  • Received:2015-05-19 Revised:2015-06-15 Published:2015-06-24
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 31101010, 21202016 and 21372038).

炔丙醇和芳基异氰在银催化条件下能够发生交叉偶联反应, 高产率地生成N-芳基-2,3-联烯酰胺. 该反应具有条件温和、原子经济性和底物范围宽泛等优点, 多种芳基异腈和炔丙醇均能发生交叉偶联反应, 并生成相应的N-芳基-2,3-联烯酰胺. 该方法解决了前期工作中异腈种类受限的问题, 为合成N-芳基联烯酰胺提供了简便新途径.

关键词: 丙炔醇, 芳基异腈, 碳酸银, 交叉偶联反应

A silver-catalyzed cross-coupling of propargylic alcohols and aryl isocyanides to N-aryl-2,3-allenamides has been developed. This reaction is both atom and step economic and applicable to a broad scope of substrates, affording a range of synthetically useful N-aryl-2,3-allenamides in good to high yields under mild conditions. This protocol has successfully solved the problem in our previous report that the isocyanides were limited to active methylene isocyanides, provided an extremely simple way to access the synthetically useful N-aryl-2,3-allenamides.

Key words: propargylic alcohols, aryl isocyanides, silver carbonate, cross-coupling reaction