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Iron/copper-catalyzed C–C cross-coupling of aryl iodides with terminal alkynes

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Pierre Vogel, Chandra Mouleeswara Rao Volla
2008

Abstract

Synergic effect of iron and copper salts as catalysts for the Sonogashira–Hagihara cross-couplings of aryl iodides with terminal alkynes is demonstrated. High yields of cross- coupled products are obtained under conditions that are smoother than those using only CuI as catalyst. Furthermore no expensive or/and toxic ligand is required.

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https://infoscience.epfl.ch/entities/publication/142a614a-4ba9-40c5-9535-de633ec191cb

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Related concepts (16)

Cross-coupling reaction

In organic chemistry, a cross-coupling reaction is a reaction where two different fragments are joined. Cross-couplings are a subset of the more general coupling reactions. Often cross-coupling reactions require metal catalysts. One important reaction type is this: (R, R' = organic fragments, usually aryle; M = main group center such as Li or MgX; X = halide) These reactions are used to form carbon–carbon bonds but also carbon-heteroatom bonds. Cross-coupling reaction are a subset of coupling reactions.

Sonogashira coupling

The Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst as well as copper co-catalyst to form a carbon–carbon bond between a terminal alkyne and an aryl or vinyl halide. R1: aryl or vinyl R2: arbitrary X: I, Br, Cl or OTf The Sonogashira cross-coupling reaction has been employed in a wide variety of areas, due to its usefulness in the formation of carbon–carbon bonds.

Catalysis (kəˈtæləsɪs) is the process of change in rate of a chemical reaction by adding a substance known as a catalyst (ˈkætəlɪst). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quickly, very small amounts of catalyst often suffice; mixing, surface area, and temperature are important factors in reaction rate. Catalysts generally react with one or more reactants to form intermediates that subsequently give the final reaction product, in the process of regenerating the catalyst.

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