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

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posted on 20.02.2015 by Jinho Kim, Shannon S. Stahl
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 Glaser–Hay 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.