Selective isomerization-carbonylation of a terpene trisubstituted double bondElectronic supplementary information (ESI) available: Detailed characterization data and data analysis. See DOI: 10.1039/c4gc01233j

Selective catalytic carbonylation of the trisubstituted double bond of citronellic acid is enabled via an isomerization-functionalization approach. Alkoxycarbonylation with [{1,2-( t Bu 2 PCH 2 ) 2 C 6 H 4 }Pd(OTf) 2 ] as a catalyst precursor occurs with >97% selectivity for the terminal diester...

Full description

Saved in:
Bibliographic Details
Main Authors Busch, Hanna, Stempfle, Florian, Heß, Sandra, Grau, Etienne, Mecking, Stefan
Format Journal Article
LanguageEnglish
Published 23.09.2014
Online AccessGet full text

Cover

More Information
Summary:Selective catalytic carbonylation of the trisubstituted double bond of citronellic acid is enabled via an isomerization-functionalization approach. Alkoxycarbonylation with [{1,2-( t Bu 2 PCH 2 ) 2 C 6 H 4 }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]. We report catalytic carbonylation of a trisubstituted double bond via an isomerization-functionalization approach.
Bibliography:10.1039/c4gc01233j
Electronic supplementary information (ESI) available: Detailed characterization data and data analysis. See DOI
ISSN:1463-9262
1463-9270
DOI:10.1039/c4gc01233j