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Selective palladium-catalyzed dehydrogenation of limonene to dimethylstyrene

Conditions for the selective dehydrogenation of (+)-limonene 1 to the polymer building block dimethylstyrene 2 are described. The reaction occurs smoothly in the presence of Pd(OTFA)2 as catalyst and CuCl2 as oxidant. High selectivity for retaining the exocyclic double bond during aromatization is a...

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Main Authors: Horrillo Martínez, Patricia (Author) , Virolleaud, Marie‐Alice (Author) , Jäkel, Christoph (Author)
Format: Article (Journal)
Language:English
Published: [February 8, 2010]
In: ChemCatChem
Year: 2010, Volume: 2, Issue: 2, Pages: 175-181
ISSN:1867-3899
DOI:10.1002/cctc.200900200
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/cctc.200900200
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/cctc.200900200
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Author Notes:Patricia Horrillo-Martínez, Marie-Alice Virolleaud, and Christoph Jaekel

MARC

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520 |a Conditions for the selective dehydrogenation of (+)-limonene 1 to the polymer building block dimethylstyrene 2 are described. The reaction occurs smoothly in the presence of Pd(OTFA)2 as catalyst and CuCl2 as oxidant. High selectivity for retaining the exocyclic double bond during aromatization is achieved (>14:1). Initially, variable-temperature NMR experiments, under stoichiometric conditions, showed a stepwise formation of a π-allyl intermediate and subsequent reaction to give a mixture of products. However, kinetic experiments showed a sigmoidal curve, pointing to the heterogeneous nature of the catalytically active species. A number of experiments were undertaken to differentiate between homogeneous, molecularly defined catalysis and heterogeneous, nanocluster-based catalysis. Based on the results, it is proposed that the true catalytic system is heterogeneous in nature. 
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