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.
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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Included in
Medicinal-Pharmaceutical Chemistry Commons, Organic Chemistry Commons, Other Chemistry Commons
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.