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

preprint
submitted on 14.02.2020 and posted on 18.02.2020 by Kiron Kumar Ghosh, Alexander Uttry, Francesca Ghiringhelli, Arup Mondal, Manuel van Gemmeren
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.

Funding

Otto Hahn Award - Max-Planck-Gesellschaft

Liebig Fellowship - Verband der Chemischen Industrie

SFB 858 - Deutsche Forschungsgemeinschaft

Doctoral Fellowship - Studienstiftung des Deutschen Volkes

History

Email Address of Submitting Author

mvangemmeren@uni-muenster.de

Institution

Westfälische Wilhelms-Universität Münster

Country

Germany

ORCID For Submitting Author

0000-0003-3080-3579

Declaration of Conflict of Interest

No conflict of interest.

Exports