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Journal Article

Direct beta-C(sp(3))-H Acetoxylation of Aliphatic Carboxylic Acids


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

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Ghosh, K. K., Uttry, A., Koldemir, A., Ong, M., & van Gemmeren, M. (2019). Direct beta-C(sp(3))-H Acetoxylation of Aliphatic Carboxylic Acids. Organic Letters, 21(17), 7154-7157. doi:10.1021/acs.orglett.9b02741.

Cite as: https://hdl.handle.net/21.11116/0000-0005-DB76-0
The controlled construction of defined oxidation patterns is one of the key aspects in the synthesis of natural products and bioactive molecules. Towards this goal, we herein report a novel protocol for the Pd-catalyzed direct beta-C(sp(3))-H acetoxylation of aliphatic carboxylic acids. The protocol enables the use of free carboxylic acids in one step and without the need of introducing specialized strong directing groups. In our studies, we found that the use of a "traceless base" was crucial for the development of a synthetically useful transformation. Furthermore, the synthetic utility of the products obtained was demonstrated by their use in subsequent transformations.