The Sonogashira cross-coupling reaction uses catalytic palladium, a copper(I)-salt, and a base to couple an organohalide and a terminal alkyne. The mechanism follows the expected oxidative addition-reductive elimination cycle, but the precise role of the Cu(I)-salt catalyst has not been fully elucidated. Good for small or large scale (>100g), this coupling is ideal for complex substrates in the late stages of a total synthesis as many functional groups are tolerated (e.g. OH, aldehyde, B(OR)2, NO2, and heterocycles).

  • Reagents: Catalytic Palladium (Pd(PPh3) 2Cl2 or Pd(PPh3)4) and Cu(I)-Salt (CuI or CuBr), Base (Et2NH, Et3N, etc.), Solvent (MeCN, THF, EtOAc)
  • Reactant: Organohalide, Terminal Alkyne
  • Product: Coupled Product
  • Type of Reaction: Acetylene Cross-Coupling


Top Citations

Original Paper

Related Reactions

  • Cadiot-Chodkiewicz Coupling
  • Stille Cross-Coupling
  • Synthesis of Substituted Alkynes
  • Synthesis of 1,3-enynes

Related Compounds

  • Organohalide
  • Catalytic Pd
  • Catalytic Cu
  • Base
By shuhan yang


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