Selective Oxidation of Alcohols to Carbonyl Compounds mediated by Fluorous-tagged TEMPO radicals (Articolo in rivista)

Type
Label
  • Selective Oxidation of Alcohols to Carbonyl Compounds mediated by Fluorous-tagged TEMPO radicals (Articolo in rivista) (literal)
Anno
  • 2005-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/adsc.200404343 (literal)
Alternative label
  • Holczknecht O.; Cavazzini M.; Quici S.; Shepperson I.;, Pozzi G. (2005)
    Selective Oxidation of Alcohols to Carbonyl Compounds mediated by Fluorous-tagged TEMPO radicals
    in Advanced synthesis & catalysis (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Holczknecht O.; Cavazzini M.; Quici S.; Shepperson I.;, Pozzi G. (literal)
Pagina inizio
  • 677 (literal)
Pagina fine
  • 688 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 347 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • CNR-Istituto di Scienze e Tecnologie Molecolari (ISTM), Via Golgi 19, 20133 Milano, Italy (literal)
Titolo
  • Selective Oxidation of Alcohols to Carbonyl Compounds mediated by Fluorous-tagged TEMPO radicals (literal)
Abstract
  • Oxidation of primary, benzylic and secondary alcohols into their corresponding aldehydes and ketones with safe, inexpensive oxidants was achieved in good yields under mild conditions in the presence of catalytic amounts of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radicals bearing perfluoroalkyl substituents. These \"fluorous-tagged\" TEMPOs were readily isolated from the reaction products by liquid-liquid or solid-phase extraction, considerably simplifying the purification step. Their recyclability was strongly influenced by the nature of the oxidizing system. The best results were obtained using either [bis(acetoxy)iodo]benzene (BAIB) or aqueous NaOCl as the primary oxidants. Fluorous TEMPO 10 could be reused up to six times in the BAIB oxidation of 1-octanol with only minor loss of catalytic activity. (literal)
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