Copper-Catalyzed Hydrative Amide Synthesis with Terminal Alkyne, Sulfonyl Azide, and Water

Citations Over TimeTop 10% of 2005 papers

Abstract

It is shown for the first time that N-sulfonyl amides can be efficiently prepared by an unconventional approach of the hydrative reaction between terminal alkynes, sulfonyl azides, and water in the presence of copper catalyst and amine base under very mild conditions. The present route is quite general, and a wide range of alkynes and sulfonyl azides are readily coupled catalytically with water to furnish amides in high yields. A variety of labile functional groups are tolerated under the conditions, and the reaction is regioselective in that only terminal alkynes react while double or internal triple bonds are intact. The reaction can be readily scaled up and is also adaptable to a solid-phase procedure with high efficiency.

Related Papers

• → Recent Advances in the Regioselective Synthesis of Pyrazoles(2011)73 cited
• → Benzotriazol-1-yl-sulfonyl Azide for Diazotransfer and Preparation of Azidoacylbenzotriazoles(2010)59 cited
• → Electronic and Steric Effects Control Regioselectivity in Alkyne Migratory Insertion during Ni-Catalyzed Indenone Synthesis(2023)4 cited
• → Visible Light Mediated Co‐Catalyzed Isocyanide Insertion with Sulfonyl Azide: Synthesis of Sulfonyl Carbamimidic Azide and Sulfonyl Aminotetrazole via Carbodiimide Intermediate(2023)1 cited
• → β-Aminoenones in the regioselective synthesis of 1,3,5-trialkylpyrazoles. The influence of the substituents in the mechanism and the regioselectivity of the reaction(1998)12 cited