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  Palladium Catalysed Acid-Free Carboxytelomerisation of 1,3-Butadiene with Alcohols Accessing Pelargonic Acid Derivatives Including Triglycerides under Selectivity Control

Vogelsang, D., Vondran, J., Hares, K., Schäfer, K., Seidensticker, T., & Vorholt, A. J. (2020). Palladium Catalysed Acid-Free Carboxytelomerisation of 1,3-Butadiene with Alcohols Accessing Pelargonic Acid Derivatives Including Triglycerides under Selectivity Control. Advanced Synthesis & Catalysis, (362), 679-687. doi:10.1002/adsc.201901383.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0006-78B0-C Version Permalink: http://hdl.handle.net/21.11116/0000-0006-78B1-B
Genre: Journal Article

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 Creators:
Vogelsang, Dennis, Author
Vondran, Johanna, Author
Hares, Kevin, Author
Schäfer, Kevin, Author
Seidensticker, Thomas, Author
Vorholt, Andreas J.1, Author              
Affiliations:
1Research Department Leitner, Max Planck Institute for Chemical Energy Conversion, Max Planck Society, ou_3023872              

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 Abstract: Palladium catalysed carboxytelomerisation of 1,3-butadiene with alcohols yields unsaturated C-9-pelargonic esters in an atom-economic and straightforward way. Although carboxytelomerisation is of current interest, limitations of applicable alcohol substrates have not been fully investigated. In here, we present the transfer of the catalytic system comprising palladium acetate and tri-n-butyl phosphine in pyridine to a broad variety of 20 alcohols with vast difference in nucleophilicity and sterical demands yielding the corresponding esters in a 100% atom economic manner. Effects of nucleophilicity and sterical demands were revealed for monoalcohols, di- and polyols. Whilst yields, chemoselectivity and E/Z-selectivity of the pelargonic acid derivatives were excellent with up to 99%, selectivity towards mono-, di- and triesters could be controlled successfully. Finally, the reaction profile of the carboxytelomerisation glycerol was uncovered, yielding up to 97% of industrially relevant unsaturated C-9-short chain fats.

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Language(s): eng - English
 Dates: 2020
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: ISI: 000501663600001
DOI: 10.1002/adsc.201901383
 Degree: -

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Title: Advanced Synthesis & Catalysis
  Abbreviation : Adv. Synth. Catal.
Source Genre: Journal
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Publ. Info: Weinheim, Fed. Rep. of Germany : Wiley-VCH Verlag GmbH
Pages: - Volume / Issue: (362) Sequence Number: - Start / End Page: 679 - 687 Identifier: ISSN: 1615-4150
CoNE: https://pure.mpg.de/cone/journals/resource/958634688013