The Castro-Stephens Coupling is an organic cross-coupling reaction between copper (I) acetylide and an aryl halide, yielding as a product a disubstituted alkyne and a copper (I) halide.
The reaction was described in 1963 by the chemists Castro and Stephens of the University of California at Riverside and is used as a tool in organic synthesis. The reaction has similarities with the synthesis of Rosenmund-von Braun (1916) and the coupling of Sonogashira (1973).
A typical reaction is the coupling of iodobenzene with copper acetylide of phenylacetylene, with pyridine reflux, to produce diphenylacetylene:
Unlike the Sonogashira coupling, the Castro-Stephens coupling produces heterocyclic compounds, when a nucleophilic group is ortho to aryl halides.
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