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

preprint
submitted on 14.02.2020, 21:24 and posted on 18.02.2020, 11:43 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