54099-19-3Relevant articles and documents
C H Bond Arylation of Diamondoids Catalyzed by Palladium(II) Acetate
Larrosa, Marta,Heiles, Sven,Becker, Jonathan,Spengler, Bernhard,Hrdina, Radim
supporting information, p. 2163 - 2171 (2016/07/16)
We have developed an effective approach to 1,2-disubstituted diamondoids by palladium(II) acetate catalyzed functionalization of C H bond. Selective mono-arylation of the adamantane framework was achieved using picolylamide as a directing group in yields up to 87 %. Kinetic studies in combination with deuterium labeling experiments, competitive experiments and mass spectrometry contribute to the mechanistic understanding of the arylation process of alkanes with number of C H bonds neighboring the directing group. Triflic anhydride promoted cyclization of the directing group generates imidazo[1,5-a]pyridine derivatives. Acid-mediated removal of the directing group provides access to 2-aryl diamondoid carboxylic acids, which are common precursors for the synthesis of various bioactive compounds (drug candidates). (Figure presented.) .