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43.6.1.3.4 Method 4: Copper/Palladium-Catalyzed Cross Coupling of Haloarenes and Terminal Alkynes (The Sonogashira–Hagihara Cross-Coupling Reaction)

DOI: 10.1055/sos-SD-043-00304

Griesbeck, A. G.; Soldevilla, A.Science of Synthesis, (200843359.

This reaction[‌60‌‌62‌] was first reported[‌63‌] by Sonogashira and Hagihara in 1975. It can be considered as an application of palladium catalysis (in the sense of the Heck reaction) to the StephensCastro reaction. Typically, two catalysts are needed for this process: a palladium(0) complex and a copper(I) halide salt. Phosphinepalladium complexes such as tetrakis(triphenylphosphine)palladium(0) are used for this process; palladium(II) complexes can also be used, as they are reduced to palladium(0) species by the consumption of terminal alkynes in the reaction medium. In contrast, copper(I) halides react with the terminal alkyne and produce copper(I) acetylide, which acts as an activated species for the coupling reactions.

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