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A general route for 13 C‐labeled fluorenols and phenanthrenols via palladium‐catalyzed cross‐coupling and one‐carbon homologation
Author(s) -
Wu Ruilian,
‘Pete’ Silks L. A.,
OlivaultShiflett Morgane,
Williams Robert F.,
Ortiz Erick G.,
Stotter Philip,
Kimball David B.,
Martinez Rodolfo A.
Publication year - 2013
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3066
Subject(s) - isotopomers , chemistry , palladium , catalysis , mass spectrometry , carbon fibers , nuclear magnetic resonance spectroscopy , coupling reaction , chemical synthesis , carbon 13 , organic chemistry , combinatorial chemistry , molecule , chromatography , biochemistry , materials science , physics , quantum mechanics , composite number , in vitro , composite material
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.