Mild Sulfonylation of Anilines

Mild Sulfonylation of Anilines

Author: ChemistryViews.org

Sulfones are functional groups often found in bioactive compounds. Their synthesis can often involve harsh conditions, which makes the late-stage functionalization of pharmaceutically active molecules difficult.

Darren J. Dixon, Robert S. Paton, Christopher J. Schofield, Martin D. Smith, Michael C. Willis, University of Oxford, UK, and colleagues have developed a mild reaction protocol for the sulfonylation of aniline derivatives with sulfinate salts. The team used [Ir(dF(CF3)ppy)2(dtbpy)]PF6 (dF(CF3)ppy = 3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl]phenyl, dtbpy = 4,4′-bis(tert-butyl)-2,2′-dipyridyl) as a photoredox catalyst, potassium persulfate as an oxidant, and blue light-emitting diodes (LEDs) to mediate the reaction.

The reaction tolerates a range of substituents on the aromatic ring and proceeds in good yields. The method is scalable and the researchers were able to demonstrate its usefulness for late-stage transformations on drugs like the antibiotic linezolid or the neuroleptic promethazine.


 

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