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Issue 18, 2016

Heterogeneous palladium-catalysed Catellani reaction in biomass-derived γ-valerolactone

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Abstract

Herein, we report the unprecedented use of a heterogeneous palladium catalyst for the step-economical Catellani reaction. The substrate scope with encapsulated Pd(OAc)2 (Pd EnCat™ 30) or Pd/Al2O3 proved to be broad, while the renewable biomass-derived γ-valerolactone (GVL) was identified as an effective reaction medium. Mechanistic studies highlighted the possible heterogeneous nature of the Pd/Al2O3 catalyst, while showing that the reaction performed in the presence of Pd EnCat™ 30 is most likely catalysed by leached homogeneous palladium species. The heterogeneous Pd/Al2O3 catalyst can be easily recovered at the end of the reaction and efficiently reused in consecutive reaction runs.

Graphical abstract: Heterogeneous palladium-catalysed Catellani reaction in biomass-derived γ-valerolactone

Supplementary files

Article information


Submitted
20 May 2016
Accepted
09 Jun 2016
First published
09 Jun 2016

This article is Open Access

Green Chem., 2016,18, 5025-5030
Article type
Paper

Heterogeneous palladium-catalysed Catellani reaction in biomass-derived γ-valerolactone

D. Rasina, A. Kahler-Quesada, S. Ziarelli, S. Warratz, H. Cao, S. Santoro, L. Ackermann and L. Vaccaro, Green Chem., 2016, 18, 5025 DOI: 10.1039/C6GC01393G

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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