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Ligand-Enabled Gold-Catalyzed C(sp2)-S Cross-Coupling Reactions
Akash G Tathe1, Nitin T Patil1
1Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal 462 066, India.
Organic Letters
|June 13, 2022
Summary
This study introduces a new gold-catalyzed reaction for creating carbon-sulfur bonds between aryl iodides and sulfonyl hydrazides. This method efficiently synthesizes important biaryl sulfones under mild conditions.
Area of Science:
- Organic Chemistry
- Catalysis
- Medicinal Chemistry
Background:
- Carbon-sulfur bond formation is crucial in synthesizing pharmaceuticals and organic materials.
- Existing cross-coupling methods often require harsh conditions or pre-functionalized substrates.
Purpose of the Study:
- To develop a novel, mild, and efficient method for C(sp2)-S cross-coupling.
- To synthesize medicinally relevant biaryl sulfones using readily available starting materials.
Main Methods:
- Ligand-enabled, gold(I)/gold(III) redox catalysis.
- Cross-coupling reaction between aryl iodides and arylsulfonyl hydrazides.
- Mechanistic studies including control experiments, mass spectrometry, and NMR spectroscopy.
Main Results:
- Successful C(sp2)-S cross-coupling achieved under mild reaction conditions.
- The protocol is effective with various aryl iodides and does not require prefunctionalized coupling partners.
- Demonstrated utility through the synthesis of diverse medicinally relevant biaryl sulfones.
Conclusions:
- A novel and efficient gold-catalyzed protocol for C(sp2)-S bond formation has been established.
- The developed method offers a practical route to valuable biaryl sulfone compounds.
- The reaction proceeds via a ligand-enabled Au(I)/Au(III) redox catalytic cycle.
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