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Ostrowski KA, Vogelsang D, Seidensticker T, et al. Direct Synthesis of an α,ω-Diester from 2,7-Octadienol as Bulk Feedstock in Three Tandem Catalytic Steps. Chemistry. 2015;22(5):1840-6doi: 10.1002/chem.201503785.
Ostrowski, K. A., Vogelsang, D., Seidensticker, T., & Vorholt, A. J. (2016). Direct Synthesis of an α,ω-Diester from 2,7-Octadienol as Bulk Feedstock in Three Tandem Catalytic Steps. Chemistry (Weinheim an der Bergstrasse, Germany), 22(5), 1840-6. https://doi.org/10.1002/chem.201503785
Ostrowski, Karoline A, et al. "Direct Synthesis of an α,ω-Diester from 2,7-Octadienol as Bulk Feedstock in Three Tandem Catalytic Steps." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,5 (2016): 1840-6. doi: https://doi.org/10.1002/chem.201503785
Ostrowski KA, Vogelsang D, Seidensticker T, Vorholt AJ. Direct Synthesis of an α,ω-Diester from 2,7-Octadienol as Bulk Feedstock in Three Tandem Catalytic Steps. Chemistry. 2016 Jan 26;22(5):1840-6. doi: 10.1002/chem.201503785. Epub 2015 Dec 22. PMID: 26691281.
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Chemistry. 2016 Jan 26;22(5):1840-6. doi: 10.1002/chem.201503785. Epub 2015 Dec 22.

Direct Synthesis of an α,ω-Diester from 2,7-Octadienol as Bulk Feedstock in Three Tandem Catalytic Steps.

Chemistry (Weinheim an der Bergstrasse, Germany)

Karoline A Ostrowski, Dennis Vogelsang, Thomas Seidensticker, Andreas J Vorholt

Affiliations

  1. Technische Universität Dortmund, Fakultät Bio- und Chemieingenieurwesen, Emil-Figgestr. 66, 44227, Dortmund, Germany.

PMID: 26691281 DOI: 10.1002/chem.201503785

Abstract

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 α,ω-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 α,ω-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.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: carbonylation; high-pressure chemistry; homogeneous catalysis; palladium; tandem catalysis

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