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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
- Improved Procedures for the Palladium-Catalyzed Coupling of Terminal Alkynes with Aryl Bromides (Sonogashira Coupling). J. Org. Chem. 1998, 63 (25), 8551–8553.
- Solvent-Free Sonogashira Coupling Reaction Viahigh Speed Ball Milling. Green Chem. 2009, 11 (11), 1821–1825.
- Cadiot-Chodkiewicz Coupling
- Stille Cross-Coupling
- Synthesis of Substituted Alkynes
- Synthesis of 1,3-enynes
- Catalytic Pd
- Catalytic Cu