Presentation Title

**Lewis Acid Mediated Synthesis of Sulfonamides from Sulfonyl Fluorides** Exemplary Presentation

Faculty Mentor

Nicholas Ball

Start Date

18-11-2017 4:10 PM

End Date

18-11-2017 4:20 PM

Location

BSC Ursa Major

Session

Exemplary

Type of Presentation

Oral Talk

Subject Area

physical_mathematical_sciences

Abstract

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.

Summary of research results to be presented

Lewis acid screens from our group and Pfizer revealed that group 2 triflamides salts significantly improve sulfonamide synthesis when using sulfonyl fluorides as a starting material. Our collaborators at Pfizer found that a wide array sulfonyl fluorides could be used to synthesize sulfonamides using Ba(NTf2)2 in water at mild temperatures with good yield (72-94%). Due to the industrial challenges of reactions in water, our group was tasked with finding a new reaction scheme using an organic solvent. We discovered with our solvent screen that t-amyl alcohol (an industrial green solvent) served as a good substitute at mild temperatures (room temperature to 60 ०C). Current amine and sulfonyl fluoride substrate scope studies suggest this method can successfully yield sulfonamides using number of different amines and sulfonyl fluorides precursors.

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Nov 18th, 4:10 PM Nov 18th, 4:20 PM

**Lewis Acid Mediated Synthesis of Sulfonamides from Sulfonyl Fluorides** Exemplary Presentation

BSC Ursa Major

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.