Cu-Catalyzed Aerobic Oxidative Three-Component Coupling Route to N-Sulfonyl Amidines via an Ynamine Intermediate

被引：70

作者：

Kim, Jinho ^{[1
]}

Stahl, Shannon S. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 04期

关键词：

ONE-POT SYNTHESIS; TERMINAL ALKYNES; EFFICIENT SYNTHESIS; SYNTHETIC UTILITY; SECONDARY-AMINES; FACILE SYNTHESIS; COPPER; AZIDES; AMIDES; HYDROAMINATION;

D O I：

10.1021/jo5029198

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cu-catalyzed aerobic oxidative three-component coupling of a terminal alkyne, secondary amine, and sulfonamide enables efficient synthesis of amidines. The use of Cu(OTf)(2) (5 mol %) produces amidines selectively without GlaserHay alkyne homocoupling products. Preliminary studies suggest that the reaction pathway involves initial oxidative coupling of the terminal alkyne with the secondary amine, followed by hydroamidation of the ynamine intermediate with the sulfonamide.

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页码：2448 / 2454

页数：7

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