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Regioselective catalytic acetoxylation of limonene

von Czapiewski, Marc; Meier, Michael A. R.

Abstract:
Two efficient strategies for a direct catalytic and regioselective acetoxylation of terpenes are described. Acetoxylated limonene derivatives were synthesized via palladium-catalyzed C-H activation utilizing para-benzoquinone (BQ) as reoxdidation agent and acetic acid as solvent and reactant. Addition of dimethyl sulfoxide (DMSO) to the catalytic system led to highly selective functionalization of the exocyclic double bond of limonene. This catalytic acetoxylation of limonene was further optimized with regard to a more sustainable and environmentally-friendly procedure. On the other hand{,} the use of an aerobic tandem catalytic system using iron(ii) phthalocyanine (Fe(Pc)) as co-catalyst{,} which acts as electron transfer mediator (ETM){,} enabled a highly selective acetoxylation of the endocyclic double bond of limonene with high conversions. Moreover{,} diacetoxylated products were prepared by a reaction sequence applying the aforementioned catalytic systems.

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Volltext §
DOI: 10.5445/IR/1000046420
Originalveröffentlichung
DOI: 10.1039/c4cy00231h
Scopus
Zitationen: 6
Web of Science
Zitationen: 5
Seitenaufrufe: 20
seit 12.05.2018
Downloads: 66
seit 19.03.2015
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Jahr 2014
Sprache Englisch
Identifikator ISSN: 2044-4753
urn:nbn:de:swb:90-464203
KITopen-ID: 1000046420
Erschienen in Catalysis Science and Technology
Band 4
Heft 8
Seiten 2318-2325
Bemerkung zur Veröffentlichung RSC geförderter Open Access-Artikel
Nachgewiesen in Web of Science
Scopus
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