Sulfonamides are an incredibly important functional group found in many of the best selling pharmaceuticals such as Viagra and Celecoxib. Most modern methods of synthesizing sulfonamides involve using sulfonyl chlorides, which require harsh reaction conditions to synthesize and in many cases are unstable. Sulfonyl fluorides are a more stable, safer alternative; however, the challenge in their application is the requirement of strong base, high temperature, or vast excess of reagents. Our lab, in conjunction with Pfizer, is developing a method that uses mild conditions to convert sulfonyl fluorides to sulfonamides using Lewis acids. We found that group 2 triflamide salts significantly enhance sulfonyl fluoride reactivity with a structurally diverse amines. We are currently involved in expanding the substrate scope to demonstrate the versatility of our method.

Lewis acid mediated synthesis of sulfonamides from sulfonyl fluorides

255th National Meeting (2018)

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