• Media type: E-Article
  • Title: A general route for 13C‐labeled fluorenols and phenanthrenols via palladium‐catalyzed cross‐coupling and one‐carbon homologation
  • Contributor: Wu, Ruilian; ‘Pete’ Silks, L. A.; Olivault‐Shiflett, Morgane; Williams, Robert F.; Ortiz, Erick G.; Stotter, Philip; Kimball, David B.; Martinez, Rodolfo A.
  • Published: Wiley, 2013
  • Published in: Journal of Labelled Compounds and Radiopharmaceuticals, 56 (2013) 11, Seite 581-586
  • Language: English
  • DOI: 10.1002/jlcr.3066
  • ISSN: 0362-4803; 1099-1344
  • Keywords: Organic Chemistry ; Spectroscopy ; Drug Discovery ; Radiology, Nuclear Medicine and imaging ; Biochemistry ; Analytical Chemistry
  • Origination:
  • Footnote:
  • Description: A series of 13C‐labeled polyaromatic hydrocarbons (PAHs), fluorenols and phenanthrenols were synthesized from commercially available 13C‐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 13C 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.