Selective isomerization-carbonylation of a terpene trisubstituted double bond

Abstract : Selective catalytic carbonylation of the trisubstituted double bond of citronellic acid is enabled via an isomerization-functionalization approach. Alkoxycarbonylation with [{1,2-((Bu2PCH2)-Bu-t)(2)C6H4}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 methonfaddition. 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].
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Submitted on : Wednesday, September 14, 2016 - 4:05:12 PM
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Hanna Busch, Florian Stempfle, Sandra Hess, Etienne Grau, Stefan Mecking. Selective isomerization-carbonylation of a terpene trisubstituted double bond . Green Chemistry, Royal Society of Chemistry, 2014, 16 (10), pp.4541-4545. ⟨10.1039/c4gc01233j ⟩. ⟨hal-01366463⟩

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