One-Pot Synthesis of Diaryl Sulfonamides via Metal Catalysis
One-Pot Synthesis of Diaryl Sulfonamides using an Iron- and Copper-Catalyzed Aryl C–H Amidation Process: L. J. N. Waddell, M. C. Henry, M. A. B. Mostafa, A. Sutherland
Synthesis 2022, DOI: 10.1055/a-1884-6988
Sulfonamides are considered privileged structures in medicinal and pharmaceutical chemistry, due to the large number of bioactive compounds – spanning a number of different therapeutic classes – incorporating a sulfonamide moiety, which is also considered a bioisosteric replacement of the amide group. A number of methods are available for the synthesis of diaryl sulfonamides, including the coupling of arylsulfonyl chlorides with anilines under basic conditions. This approach is highly effective, but it requires the synthesis and handling of sulfonyl chlorides, which are often very toxic. Recently, the group of Professor Andrew Sutherland (University of Glasgow, UK) reported a new one-pot entry to the title compounds, based on the use of a Fe- and Cu-catalyzed aryl C–H amidation between activated aromatic compounds (anisoles, anilines and acetanilides) and primary sulfonamides.
Professor Sutherland said: “This method allows the one-pot synthesis of pharmaceutically relevant diaryl sulfonamides from activated arenes using earth-abundant transition metal catalysis.”