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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Aromatic Chlorosulfonylation by Photoredox Catalysis
Michal Májek1, Michael Neumeier1, Axel Jacobi von Wangelin1
1Institute of Organic Chemistry, University of Regensburg, Universitätsstr. 31, 93040, Regensburg, Germany.
Visible-light photoredox catalysis offers an efficient method for synthesizing arenesulfonyl chlorides from anilines. This new protocol uses readily available precursors under mild conditions, tolerating diverse functional groups.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Arenesulfonyl chlorides are valuable synthetic intermediates.
- Traditional methods for their synthesis often require harsh conditions or specialized reagents.
Purpose of the Study:
- To develop an efficient and mild method for arenesulfonyl chloride synthesis.
- To utilize visible-light photoredox catalysis for this transformation.
Main Methods:
- In situ generation of arenediazonium salts from anilines.
- Generation of sulfur dioxide (SO2) and hydrogen chloride (HCl) from aqueous thionyl chloride (SOCl2).
- Visible-light photocatalysis in acetonitrile/water at room temperature.
Main Results:
- Successful synthesis of arenesulfonyl chlorides from anilines.
- The reaction proceeds under mild conditions with low catalyst loading.
- High functional group tolerance, including halides, azides, nitro groups, CF3, SF5, esters, and heteroarenes.
Conclusions:
- Visible-light photoredox catalysis provides an effective route to arenesulfonyl chlorides.
- The developed protocol is convenient, mild, and broadly applicable.
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