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Castro–Stephens coupling

Robert D. Stephens The Castro–Stephens coupling is a cross coupling reaction between a copper(I) acetylide and an aryl halide in pyridine, forming a disubstituted alkyne and a copper(I) halide.

:[[File:General scheme for Castro-Stephens coupling.png|700px|General scheme for Castro-Stephens coupling]]

The reaction was described in 1963 by chemists Castro and Stephens. The reaction is similar to the much older Rosenmund–von Braun synthesis (1914) between aryl halides and copper(I) cyanide and was itself modified in 1975 as the Sonogashira coupling by adding a palladium catalyst and preparing the organocopper compound in situ, allowing copper to also be used catalytically.

A typical reaction diphenylacetylene is obtained by the coupling of iodobenzene with CuC2C6H5 in hot pyridine:

:[[Image:Castro-Stephens application.png|650px|Application of Castro–Stephens coupling with phenyliodide.]]

Unlike the Sonogashira coupling, the Castro–Stephens coupling can produce heterocyclic compounds when a nucleophilic group is ortho to the aryl halide, although this typically requires use of dimethylformamide (DMF) as solvent.

:[[File:Castro-Stephens 3-n-Propylisocoumarin synthesis.png|700px|Application of Castro-Stephens coupling with o-iodobenzoic acid to produce an isocoumarin.]]

References

References

  1. (1963). "The Substitution of Aryl Iodides with Cuprous Acetylides. A Synthesis of Tolanes and Heterocyclics". [[J. Org. Chem.]].
  2. (1972). "Substitution of Aryl Halides with Copper(I) Acetylides: 2-Phenylfuro[3,2-''b'']pyridine".
  3. (1919). "Das am Ringkohlenstoff gebundene Halogen und sein Ersatz durch andere Substituenten. I. Mitteilung: Ersatz des Halogens durch die Carboxylgruppe". [[Ber. Dtsch. Chem. Ges. A/B]].
  4. (1931). "Fluoranthen und seine Derivate. III. Mitteilung". [[Justus Liebigs Ann. Chem.]].
  5. (1975). "A convenient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines". [[Tetrahedron Lett.]].
  6. Sonogashira, Kenkichi. (2002). "Development of Pd-Cu catalyzed cross-coupling of terminal acetylenes with sp2-carbon halides". [[J. Organomet. Chem.]].
  7. (1980). "Synthesis of natural isocoumarins, artemidin and 3-propylisocoumarin". [[J. Org. Chem.]].
  8. (1969). "Copper(I) Substitutions. Scope and Mechanism of Cuprous Acetylide Substitutions". [[J. Am. Chem. Soc.]].
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