A general route for13C-labeled fluorenols and phenanthrenols via palladium-catalyzed cross-coupling and one-carbon homologation

Autor: L. A. 'Pete' Silks, Ruilian Wu, Erick G. Ortiz, Robert F. Williams, Morgane Olivault-Shiflett, David B. Kimball, Philip L. Stotter, Rodolfo A. Martinez
Rok vydání: 2013
Předmět:
Zdroj: Journal of Labelled Compounds and Radiopharmaceuticals. 56:581-586
ISSN: 0362-4803
DOI: 10.1002/jlcr.3066
Popis: A series of (13)C-labeled polyaromatic hydrocarbons (PAHs), fluorenols and phenanthrenols were synthesized from commercially available (13)C-labeled starting material giving rise to M + 6 isotopomers. This was accomplished using key palladium-catalyzed cross-coupling and one-carbon homologation strategies. The conditions for these reactions were optimized, and the new chemical routes are efficient in the number of chemical steps, can be scaled to afford gram quantities and occur in good yields based on the (13)C label. These labeled compounds as precursors for more complex PAHs and are useful as internal standards in mass spectrometry and NMR spectroscopy studies for monitoring environmental contamination and biological exposure to PAHs and their metabolites.
Databáze: OpenAIRE