Hydroamination of Propiolic Derivatives with N-Fluorobenzene-sulfonimide Catalyzed by Silver Carbonate

doi:10.6023/cjoc201912001

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (5): 1310-1315.DOI: 10.6023/cjoc201912001 Previous Articles Next Articles

碳酸银催化N-氟代二苯磺酰亚胺与丙炔酸衍生物的氢胺化反应

任海平, 田再文, 李柯, 张万轩

湖北大学有机化工新材料湖北省协同创新中心有机功能分子合成与应用教育部重点实验室武汉 430062

收稿日期:2019-12-01 修回日期:2020-01-09 发布日期:2020-01-21
通讯作者: 张万轩 E-mail:zhangwx@hubu.edu.cn
基金资助:
有机功能分子合成与应用教育部重点实验室资助项目（No.KLSAOFM1912）.

Hydroamination of Propiolic Derivatives with N-Fluorobenzene-sulfonimide Catalyzed by Silver Carbonate

Ren Haiping, Tian Zaiwen, Li Ke, Zhang Wanxuan

Hubei Collaborative Innovation Center for Advanced Organic Chemical Material, Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Ministry of Education, Hubei University, Wuhan 430062

Received:2019-12-01 Revised:2020-01-09 Published:2020-01-21
Supported by:
Project supported by the Key Laboratory for the Synthesis and Applicationof Organic Functional Molecules, Ministry of Education (No. KLSAOFM1912).

1. 201310S.pdf(1758KB)

Abstract

Amination using N-fluorobenzenesulfonimide (NFSI) as nitrogen source has become an important route to prepare amines. However, there are few methods to prepare N-vinyl sulfonimides using NFSI as nitrogen source. In the presence of Na₂HPO₄, the hydroamination of propiolates or propiolamides with N-fluorobenzenesulfonimide (NFSI) was realized, where Ag₂CO₃ and 1,10-phenanthroline derivatives were added as catalysts. It leads to N-vinyldibenzenesulfonimides in high selectivity of Z isomers in the yields of 35%~71%.

Key words: silver carbonate, N-fluorobenzenesulfonimide, N-vinyldibenzenesulfonimide, propiolate, propiolamide

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Ren Haiping, Tian Zaiwen, Li Ke, Zhang Wanxuan. Hydroamination of Propiolic Derivatives with N-Fluorobenzene-sulfonimide Catalyzed by Silver Carbonate[J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1310-1315.

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碳酸银催化N-氟代二苯磺酰亚胺与丙炔酸衍生物的氢胺化反应

Hydroamination of Propiolic Derivatives with N-Fluorobenzene-sulfonimide Catalyzed by Silver Carbonate

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