Description/Abstract/Artist Statement

The selective oxidation of thiols to disulfides is an area of great importance in the areas of materials and medicinal chemistry research. The production of polymers, rubber, pharmaceuticals, and the folding of proteins in biological systems all rely on the formation of disulfide bonds. Herein, we introduce a stoichiometric and electrocatalytic method for the oxidation of various pharmaceutically and biologically relevant thiols into their respective disulfides in more environmentally benign solvents such as water and alcohol solvents. The scope of the transformation was evaluated and a detailed mechanistic study involving control experiments, experimental kinetic studies, and computational investigations led to new insights into how the oxidation takes place via an unusual anionic process.

Presenting Author Name/s

Kosta V. Vlasakakis, Olivia M. White

Faculty Advisor/Mentor

Kyle M. Lambert

College Affiliation

College of Sciences

Presentation Type

Poster

Disciplines

Chemistry | Medicinal-Pharmaceutical Chemistry | Organic Chemistry | Other Chemistry

Session Title

Poster Session

Location

Learning Commons @ Perry Library

Start Date

3-19-2022 9:00 AM

End Date

3-19-2022 11:00 AM

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Mar 19th, 9:00 AM Mar 19th, 11:00 AM

Oxidation of Thiols to Disulfides using an Environmentally “Green” Organocatalyst and New Mechanistic Insights

Learning Commons @ Perry Library

The selective oxidation of thiols to disulfides is an area of great importance in the areas of materials and medicinal chemistry research. The production of polymers, rubber, pharmaceuticals, and the folding of proteins in biological systems all rely on the formation of disulfide bonds. Herein, we introduce a stoichiometric and electrocatalytic method for the oxidation of various pharmaceutically and biologically relevant thiols into their respective disulfides in more environmentally benign solvents such as water and alcohol solvents. The scope of the transformation was evaluated and a detailed mechanistic study involving control experiments, experimental kinetic studies, and computational investigations led to new insights into how the oxidation takes place via an unusual anionic process.