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Ligand-Enabled γ-C(sp3)–H Olefination of Free Carboxylic Acids

18 February 2020, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We report the ligand enabled C(sp3)–H activation/olefination of free carboxylic acids in the γ-position. Through an intramolecular Michael-addition, δ-lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium-catalyzed activation of free carboxylic acids in the γ-position. The developed protocol features a wide range of acid substrates and olefin reaction partners and is shown to be applicable on a preparatively useful scale. Insights into the underlying reaction mechanism obtained through kinetic studies are reported.

Keywords

γ-C(sp3)–H activation
Carboxylic AcidsA
δ-Lactones
Ligand-Enabled Catalysis
Palladium

Supplementary materials

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Description
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Title
Ghosh Uttry et al olefination SI
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Now Published

Ligand‐Enabled γ‐C(sp3)−H Olefination of Free Carboxylic Acids [opens in a new tab]
Kiron Kumar Ghosh, Alexander Uttry, Arup Mondal, Francesca Ghiringhelli, Philipp Wedi, Manuel van Gemmeren journal article
Angewandte Chemie International Edition , Volume 59, Issue 31
Online publication date: May 18, 2020

Version History

Feb 18, 2020 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.11857857.v1
D O I: 10.26434/chemrxiv.11857857.v1 [opens in a new tab]

Funding

Otto Hahn Award - Max-Planck-Gesellschaft
Liebig Fellowship - Verband der Chemischen Industrie
SFB 858 - Deutsche Forschungsgemeinschaft
Doctoral Fellowship - Studienstiftung des Deutschen Volkes

Author’s competing interest statement

No conflict of interest.

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