N‑Boryl Pyridyl Radical-Mediated Reductive Homocoupling of Arylsulfonyl Chlorides to Diaryl Disulfides
Yuan-Kai Cheng, Chien-Miao Li, Woo-Jin Yoo
TL;DR
A new method uses radicals to convert arylsulfonyl chlorides into diaryl disulfides efficiently.
Contribution
A novel reductive homocoupling method using N-boryl pyridyl radicals is introduced for diaryl disulfide synthesis.
Findings
Arylsulfonyl chlorides can be converted into symmetrical diaryl disulfides using a 4-cyanopyridine catalyst.
The reaction proceeds via arylsulfonyl radicals and single-electron reductions mediated by N-boryl pyridyl radicals.
The method allows for the synthesis of a variety of diaryl disulfides under mild conditions.
Abstract
Arylsulfonyl chlorides were found to undergo 4-cyanopyridine-catalyzed, bis(pinacolato)diboron-mediated reductive homocoupling to afford a variety of symmetrical diaryl disulfides. Preliminary mechanistic studies suggest that arylsulfonyl radicals are involved and that diaryl disulfide formation likely proceeds through successive single-electron reductions mediated by N-boryl pyridyl radicals.
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Taxonomy
TopicsSulfur-Based Synthesis Techniques · Catalytic C–H Functionalization Methods · Radical Photochemical Reactions