Nitro-sulfinate Reductive Coupling to Access (Hetero)aryl Sulfonamides.
Sandra E Gatarz1, Oliver M Griffiths1, Henrique A Esteves1
1Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, U.K.
Researchers developed a new method for synthesizing sulfonamides using reductive coupling of aryl sulfinates and nitroarenes. This ultrasound-assisted approach offers an efficient route to diverse sulfonamide compounds.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Sulfonamides are crucial pharmacophores found in numerous drugs.
- Efficient synthetic routes for diverse sulfonamide scaffolds are highly sought after.
Purpose of the Study:
- To report a novel method for synthesizing (hetero)aryl sulfonamides.
- To explore reductive coupling of aryl sulfinates and nitroarenes.
Main Methods:
- Utilized reductive coupling of aryl sulfinates and nitroarenes.
- Employed sodium bisulfite as a reducing agent, with or without tin(II) chloride.
- Incorporated an ultrasound bath to enhance reaction homogeneity and mixing.
- Investigated various reaction conditions in dimethyl sulfoxide (DMSO).
Main Results:
- Successfully synthesized a range of (hetero)aryl sulfonamides with diverse functional groups.
- Established the mechanism of the transformation, proposing nitrosoarene intermediates.
- Confirmed nitrosoarene intermediate formation via an independent molecular coupling strategy.
Conclusions:
- The developed method provides an efficient pathway to (hetero)aryl sulfonamides.
- The study elucidates the reaction mechanism, highlighting the role of nitrosoarene intermediates.
- This work contributes a valuable synthetic tool for medicinal and organic chemistry.
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