Issue 10, 2014
From the journal:

Green Chemistry

Selective isomerization–carbonylation of a terpene trisubstituted double bond†

Hanna Busch,a   Florian Stempfle,a   Sandra Heß,a   Etienne Graua  and  Stefan Mecking*a  

* Corresponding authors

a Chair of Chemical Materials Science, Department of Chemistry, University of Konstanz, 78464 Konstanz, Germany
E-mail: stefan.mecking@uni-konstanz.de
Fax: +49 7531 88-5152
Tel: +49 7531 88-5151

Abstract

Selective catalytic carbonylation of the trisubstituted double bond of citronellic acid is enabled via an isomerization–functionalization approach. Alkoxycarbonylation with [{1,2-(tBu2PCH2)2C6H4}Pd(OTf)2] as a catalyst precursor occurs with >97% selectivity for the terminal diester dimethyl-3,7-dimethylnonane-dioate. This prevails much over the typical cationic methoxyaddition. The reactive primary carboxy group formed allows for e.g. the preparation of the high molecular weight novel polyester poly[3,7-dimethylnonanediyl-3,7-dimethylnonanedioate].

Graphical abstract: Selective isomerization–carbonylation of a terpene trisubstituted double bond

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Article information

DOI
https://doi.org/10.1039/C4GC01233J
Article type
Communication
Submitted
02 Jul 2014
Accepted
18 Aug 2014
First published
03 Sep 2014

Green Chem., 2014,16, 4541-4545

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Selective isomerization–carbonylation of a terpene trisubstituted double bond

H. Busch, F. Stempfle, S. Heß, E. Grau and S. Mecking, Green Chem., 2014, 16, 4541 DOI: 10.1039/C4GC01233J

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