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Directed C−H Bond Oxidation of Bridged Cycloalkanes Catalyzed by Palladium(II) Acetate
Author(s) -
Larrosa Marta,
Zonker Benjamin,
Volkmann Jannis,
Wech Felix,
Logemann Christian,
Hausmann Heike,
Hrdina Radim
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800550
Subject(s) - adamantane , cycloalkane , palladium , chemistry , catalysis , ligand (biochemistry) , substrate (aquarium) , surface modification , bond cleavage , organic chemistry , medicinal chemistry , polymer chemistry , combinatorial chemistry , biochemistry , oceanography , receptor , geology
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 3 ‐tri‐substituted adamantane derivatives was achieved.