Synthesis of triphenylsilyl(~(14)C_2)acetylene for use in a Sonogashira reaction

摘要

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.