mechanism | organic synthesis | chemical biology
Synthetic Radical Chemistry
Just when you think you’ve mastered organic chemistry, along comes sulfur. Organosulfur compounds often engage in reactivity that defies the conventional intuition of organic chemists, making it a fertile playground for new reactivity. Our group first became enamored by the magic of sulfur while studying the antioxidant activity of allicin, the origin of garlic’s characteristic odour. We have since pursued a variety of projects aimed at understanding the potent H-atom transfer activity of organosulfur compounds and radical substitution chemistry on polysulfide species, to enable synthetic method development and understand their important antioxidant activity. We have also aimed to shed light on the various mechanisms by which thiols undergo oxidation, as this is key to the role of amino acid cysteine in protein structure/function and cell signaling processes.
Check out some representative work from our lab:
A Divergent Strategy for Site-Selective Radical Disulfuration
of Carboxylic Acids with Trisulfide-1,1-Dioxides
Zijun Wu & Derek A. Pratt*
Angewandte Chemie International Edition 2021, 60, 15598-15605
Radical Substitution on Tetrasulfides: A Unique Route to Disulfides
Zijun Wu & Derek A. Pratt*
Journal of the American Chemical Society 2020, 142, 10284-10290
The Antioxidant Activity of Polysulfides: It’s Radical!
Jean-Philippe R. Chauvin, Markus Griesser & Derek A. Pratt*
Chemical Science 2019, 10, 4999-5010
The Hydrogen Atom Transfer Reactivity of Sulfinic Acids
Markus Griesser, Jean-Philippe R. Chauvin & Derek A. Pratt*
Chemical Science 2018, 9, 7218-7229
Hydroperosulfides: H-atom Transfer Agents Par Excellence
Jean-Philippe R. Chauvin, Markus Griesser & Derek A. Pratt*
Journal of the American Chemical Society 2017, 139, 6484-6493
On the Mechanism of Thiol, Sulfenic and Sulfinic Acid Oxidation by Hydrogen Peroxide
Jean-Philippe R. Chauvin & Derek A. Pratt*
Angewandte Chemie International Edition 2017, 56, 6255-6259
