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Synthesis of triphenylsilyl[ 14 C 2 ]acetylene for use in a Sonogashira reaction
Author(s) -
Elmore Charles S.,
Dorff Peter N.
Publication year - 2011
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.1808
Subject(s) - synthon , sonogashira coupling , chemistry , acetylene , yield (engineering) , halide , aryl , phenylacetylene , medicinal chemistry , organic chemistry , combinatorial chemistry , palladium , catalysis , alkyl , materials science , metallurgy
Silylacetylenes are useful coupling partners for aromatic halides in the Sonogashira reaction and a C‐14 labeled version of this useful synthon would allow ready access to a wide variety of arylalkynes. Ca 14 C 2 was converted to triphenylsilyl[ 14 C 2 ]acetylene using two related routes in 65% yield, and the resulting [ 14 C 2 ]acetylene was coupled with an aryl halide to give the target triphenylsilylarylacetylene (2) in 40% yield. Copyright © 2010 John Wiley & Sons, Ltd.
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