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Ligand-Enabled gamma-C(sp(3))-H Olefination of Free Carboxylic Acids

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Mondal,  Arup
Research Department Schlögl, Max Planck Institute for Chemical Energy Conversion, Max Planck Society;

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Wedi,  Philipp
Research Department Schlögl, Max Planck Institute for Chemical Energy Conversion, Max Planck Society;

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van Gemmeren,  Manuel
Research Department Schlögl, Max Planck Institute for Chemical Energy Conversion, Max Planck Society;

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Citation

Ghosh, K. K., Uttry, A., Mondal, A., Ghiringhelli, F., Wedi, P., & van Gemmeren, M. (2020). Ligand-Enabled gamma-C(sp(3))-H Olefination of Free Carboxylic Acids. Angewandte Chemie, International Edition in English, 59(31), 12848-12852. doi:10.1002/anie.202002362.


Cite as: http://hdl.handle.net/21.11116/0000-0007-A700-C
Abstract
We report the ligand-enabled C-H activation/olefination of free carboxylic acids in the gamma-position. Through an intramolecular Michael addition, delta-lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium-catalyzed activation of free carboxylic acids in the gamma-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.