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

Authors :: Larrosa M
Zonker B
Volkmann J
Wech F
Logemann C
Hausmann H
Hrdina R
Source :: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2018 Apr 20; Vol. 24 (23), pp. 6269-6276. Date of Electronic Publication: 2018 Mar 22.
Publication Year :: 2018
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-C <subscript>3</subscript> -tri-substituted adamantane derivatives was achieved.<br /> (© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

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