Synthesis of N-sulfonamidines via three-component coupling using heterogeneous copper catalysts

High-Yield Synthesis of N-Sulfonamidines Using Reusable MOF-Derived Copper Catalysts

This technology provides a method for synthesizing N-sulfonamidines via a three-component coupling reaction of terminal alkynes, sulfonyl azides, and amines, utilizing a heterogeneous catalyst (Cu@C) prepared by the pyrolysis of the metal-organic framework HKUST-1 to support copper on carbon.

Amidines are essential building blocks for heterocyclic compounds and bioactive substances, but conventional synthesis has relied on functional group transformation of precursors like nitriles and aldoximes. While copper-catalyzed three-component reactions have been reported, they primarily use homogeneous catalysts, which are difficult to recover and reuse after the reaction.

This technology performs the reaction using a Cu@C catalyst in an acetonitrile solvent under a nitrogen atmosphere, achieving high yields of N-sulfonamidines across various substrates. The catalyst is easily recovered via centrifugation and can be reused at least four times without loss of activity. Applicable to the production of pharmaceutical intermediates and fine chemical building blocks, it reduces both the consumption of expensive copper catalysts and the burden of separation processes.

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Key Features:

• A method for synthesizing N-sulfonamidine compounds through a three-component coupling reaction of terminal alkyne compounds, sulfonyl azide compounds, and amine compounds
• A configuration using a heterogeneous copper catalyst (Cu@C) prepared by pyrolyzing HKUST-1 to support copper on a carbon substrate
• A process performed in an acetonitrile solvent under nitrogen supply, including a step of adding triethylamine first when using ammonia
• A synthesis method using 2.5–5 mol% of the heterogeneous copper catalyst relative to the terminal alkyne, maintaining a reaction yield of over 80% even upon reuse

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