4.5 Article

Synthesis of Sulfones by Iron-Catalyzed Decomposition of Sulfonylhydrazones

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 8, Pages 1520-1526

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001492

Keywords

Sulfur; Hydrazones; Iron; Cross-coupling; Diazo compounds; Carbenes

Funding

  1. Direccion General de Investigacion (DGI) of Spain [CTQ2007-61048/BQU]
  2. Consejeria de Educacion y Ciencia of Principado de Asturias [IB08-088]

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The Fe-catalyzed decomposition of sulfonylhydrazones gives rise to sulfones. The reaction is quite general and allows the preparation of sulfones from a variety of aryl, alkyl, and a, alpha,beta-unsaturated aldehydes and ketones. Crossover experiments reveal that the reaction is an intermolecular process, which may proceed by nucleophilic attack of the sulfinate anion on an iron carbene complex.

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