Selective isomerization-carbonylation of a terpene trisubstituted double bond

Busch, Hanna; Stempfle, Florian; Hess, Sandra K.; Grau, Etienne; Mecking, Stefan

Selective isomerization-carbonylation of a terpene trisubstituted double bond

Dateien

Busch_0-258649.pdfGröße: 287.37 KBDownloads: 627

Datum

2014

Autor:innen

Grau, Etienne

Open Access-Veröffentlichung

Open Access Green

Sammlungen

Chemie

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

Green Chemistry. 2014, 16(10), pp. 4541-4545. ISSN 1463-9262. eISSN 1463-9270. Available under: doi: 10.1039/C4GC01233J

Zusammenfassung

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].

Fachgebiet (DDC)

540 Chemie

Zitieren

ISO 690

BUSCH, Hanna, Florian STEMPFLE, Sandra K. HESS, Etienne GRAU, Stefan MECKING, 2014. Selective isomerization-carbonylation of a terpene trisubstituted double bond. In: Green Chemistry. 2014, 16(10), pp. 4541-4545. ISSN 1463-9262. eISSN 1463-9270. Available under: doi: 10.1039/C4GC01233J

BibTex

@article{Busch2014Selec-29312,
  year={2014},
  doi={10.1039/C4GC01233J},
  title={Selective isomerization-carbonylation of a terpene trisubstituted double bond},
  number={10},
  volume={16},
  issn={1463-9262},
  journal={Green Chemistry},
  pages={4541--4545},
  author={Busch, Hanna and Stempfle, Florian and Hess, Sandra K. and Grau, Etienne and Mecking, Stefan}
}

RDF

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    <dcterms:abstract xml:lang="eng">Selective catalytic carbonylation of the trisubstituted double bond of citronellic acid is enabled via an isomerization–functionalization approach. Alkoxycarbonylation with [{1,2-(&lt;sup&gt;t&lt;/sup&gt;Bu&lt;sub&gt;2&lt;/sub&gt;PCH&lt;sub&gt;2&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;C&lt;sub&gt;6&lt;/sub&gt;H&lt;sub&gt;4&lt;/sub&gt;}Pd(OTf)&lt;sub&gt;2&lt;/sub&gt;] as a catalyst precursor occurs with &gt;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].</dcterms:abstract>
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