Journal article

Publication year: 2016

Pages: 2163-2171

Journal: Advanced Synthesis & Catalysis

Volume number: 358

Issue number: 13

ISSN: 1615-4150

DOI Link: https://doi.org/10.1002/adsc.201600156

Publisher: Wiley

Abstract: 
We have developed an effective approach to 1,2-disubstituted diamondoids by palladium(II) acetate catalyzed functionalization of CH 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 CH 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).

Harvard Citation style: Larrosa, M., Heiles, S., Becker, J., Spengler, B. and Hrdina, R. (2016) CH Bond Arylation of Diamondoids Catalyzed by Palladium(II) Acetate, Advanced Synthesis & Catalysis, 358(13), pp. 2163-2171. https://doi.org/10.1002/adsc.201600156

APA Citation style: Larrosa, M., Heiles, S., Becker, J., Spengler, B., & Hrdina, R. (2016). CH Bond Arylation of Diamondoids Catalyzed by Palladium(II) Acetate. Advanced Synthesis & Catalysis. 358(13), 2163-2171. https://doi.org/10.1002/adsc.201600156