Rhodium-Catalyzed Hydroformylation of 1,1-Disubstituted Allenes Employing the Self-Assembling 6-DPPon System

A rhodium‐catalyzed hydroformylation of 1,1‐disubstituted allenes is reported. Using a RhI/6‐DPPon catalyst system, one can obtain β,γ‐unsaturated aldehydes in high regio‐ and chemoselectivity. The Z‐configured product is formed with up to >95 % selectivity when unsymmetrically 1,1‐disubstituted...

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Bibliographic Details
Published in:Angewandte Chemie 2015-06, Vol.127 (23), p.7017-7021
Main Authors: Köpfer, Alexander, Breit, Bernhard
Format: Article
Language:eng ; ger
Subjects:
Accessibility
Aldehyde
Aldehydes
Allene
Catalysts
Chemistry
Hydroformylierungen
Methodology
Rhodium
Selbstorganisation
Selectivity
Transformations
Utilities
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Summary:A rhodium‐catalyzed hydroformylation of 1,1‐disubstituted allenes is reported. Using a RhI/6‐DPPon catalyst system, one can obtain β,γ‐unsaturated aldehydes in high regio‐ and chemoselectivity. The Z‐configured product is formed with up to >95 % selectivity when unsymmetrically 1,1‐disubstituted allenes are submitted to the reaction conditions. This is the first time that these interesting building blocks are accessible by hydroformylation of allenes. The utility of this methodology is demonstrated by further transformations of one of the obtained products. β,γ‐Ungesättigte Aldehyde werden durch rhodiumkatalysierte Hydroformylierung von 1,1‐disubstituierten Allenen erhalten. Bei unsymmetrisch 1,1‐disubstituierten Allenen wird das Z‐konfigurierte Produkt mit bis zu >95 % Selektivität gebildet. Dies ist die erste Synthese solcher Bausteine durch Hydroformylierung von Allenen. Der Nutzen dieser Methode wurde durch Folgechemie eines der erhaltenen Produkte demonstriert.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201502086