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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

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