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Issue 8, 2014
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Regioselective catalytic acetoxylation of limonene

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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.

Graphical abstract: Regioselective catalytic acetoxylation of limonene

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Publication details

The article was received on 20 Feb 2014, accepted on 29 Apr 2014 and first published on 30 Apr 2014


Article type: Paper
DOI: 10.1039/C4CY00231H
Citation: Catal. Sci. Technol., 2014,4, 2318-2325
  • Open access: Creative Commons BY license
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    Regioselective catalytic acetoxylation of limonene

    M. von Czapiewski and M. A. R. Meier, Catal. Sci. Technol., 2014, 4, 2318
    DOI: 10.1039/C4CY00231H

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