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Directed C-H Bond Oxidation of Bridged Cycloalkanes Catalyzed by Palladium(II) Acetate

Marta Larrosa, Benjamin Zonker, Jannis Volkmann, Felix Wech, Christian Logemann, Heike Hausmann, Radim Hrdina

Chemistry. 2018 Apr 20;24(23):6269-6276.

PMID: 29488690

Abstract:

We have developed a synthesis of 1,2-substituted adamantane carboxylic acids and further bridged cycloalkanes (cage compounds) by palladium acetate-catalyzed C-H bond oxidation. Acetoxylation of cycloalkane framework was performed using picolylamide as a directing group. Modification of the substrate, ligand design and variation of reaction conditions enabled us to study the mechanism of acetoxylation of aliphatic compounds. Post-functionalization reactions and cleavage of the directing group were developed. For the first time the synthesis and characterization of a β-C3 -tri-substituted adamantane derivatives was achieved.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP3375313 Palladium(II) acetate Palladium(II) acetate 3375-31-3 Price
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