The sulfonamide moiety is an important bioisostere found in a wide range of pharmaceuticals. New synthetic methods for the direct installation of sulfonamides are desired for discovery and development of new bioactive compounds. The most common method of sulfonamide incorporation typically involves the use of a pre-installed amine and sulfonyl chloride under basic conditions. Sulfonamide installation at a carbonyl resulting in the formation of an intermediate imine is an alternative method. These imine-forming methods utilize high temperatures, costly catalysts, or acidic conditions. This results in limited substrate scope when it comes to acid-sensitive compounds containing a basic site capable of coordinating a Lewis or Bronsted acid. A new approach for the direct installation of sulfonamides using either an iminoiodinane/I2 or sulfonamide/iodobenzene diacetate/I2 system to form N-sulfonyl imine intermediate from aryl and/or heteroaryl aldehydes under mild conditions has been developed. These intermediate imines can then be reduced (one pot) in a second step to form N-benzylsulfonamides. This method is non-metal promoted, does not require removal of water, operates under mild reaction temperatures, and can be used for a wide range of substrates including acid-sensitive compounds. Our recent progress regarding the development of a method for installation of N-sulfonyl units at carbonyls, along with results from a cytotoxicity screening and viability investigation of a library of synthesized compounds will be presented.

Hypervalent iodine reagent-mediated formation of bioactive N-benzylsulfonamides from aryl and heteroaryl aldehydes

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.