Direct Synthesis of an [alpha],[omega]-Diester from 2,7-Octadienol as Bulk Feedstock in Three Tandem Catalytic Steps

A new tandem catalytic process was designed and developed as a tool for the direct conversion of the widely available feedstock 2,7-octadienol into an [alpha],[omega]-diester. This innovative auto-tandem catalysis is atom efficient and consists of three consecutive palladium-catalysed reactions: eth...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-01, Vol.22 (5), p.1840
Main Authors: Ostrowski, Karoline A, Vogelsang, Dennis, Seidensticker, Thomas, Vorholt, Andreas J
Format: Article
Language:English
Subjects:
Carbonyls
Cascade chemical reactions
Catalysis
Chemistry
Design
Design of experiments
Design parameters
Direct conversion
Ligands
Mathematical models
Nucleotide sequence
Palladium
Raw materials
Substrates
Yield
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Summary:A new tandem catalytic process was designed and developed as a tool for the direct conversion of the widely available feedstock 2,7-octadienol into an [alpha],[omega]-diester. This innovative auto-tandem catalysis is atom efficient and consists of three consecutive palladium-catalysed reactions: ether formation, ether carbonylation and alkoxycarbonylation. By using the design of experiments (DoE) approach, significant parameters were determined and the yield of the desired [alpha],[omega]-diester was optimised. Model substrates allowed deeper insight into the progress of the reaction to be gained and, as a result, the reaction sequence was uncovered. Furthermore, by simply applying other ligands, a different reaction path was followed, allowing other, new tandem catalytic sequences to be explored and enabling new compounds to be obtained.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201503785