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

doi:10.6023/cjoc201505025

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (10): 2095-2101.DOI: 10.6023/cjoc201505025 Previous Articles Next Articles

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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

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 Wenshuai^a, Zhao Shoujing^a, Luo Xiaopei^a, Song Jinna^a, Liu Jianquan^b, Bi Xihe^b, Liao Peiqiu^b

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).

1. Silver-Catalyzed Cross-Coupling Reaction of Propargylic Alcohols and Arylisocyanides: An Atom-Economic Synthesis of N-Aryl-2,3-allenamides.PDF(1485KB)

Abstract

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

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Xu Wenshuai, Zhao Shoujing, Luo Xiaopei, Song Jinna, Liu Jianquan, Bi Xihe, Liao Peiqiu. Silver-Catalyzed Cross-Coupling Reaction of Propargylic Alcohols and Arylisocyanides: An Atom-Economic Synthesis of N-Aryl-2,3-allenamides[J]. Chin. J. Org. Chem., 2015, 35(10): 2095-2101.

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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

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

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