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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:
The most common type of coupling reaction is the cross coupling reaction. [1] [2] [3] Richard F. Heck, Ei-ichi Negishi, and Akira Suzuki were awarded the 2010 Nobel Prize in Chemistry for developing palladium-catalyzed cross coupling reactions. [4] [5] Broadly speaking, two types of coupling reactions are recognized:
Both palladium and copper complexes of the compound exhibit high activity for the coupling of aryl halides and aryl tosylates with various amides. [1] It is also an efficient ligand for several commonly used C–C bond-forming cross-coupling reactions, including the Negishi, Suzuki, and the copper-free Sonogashira coupling reactions.
The Hiyama coupling is a palladium-catalyzed cross-coupling reaction of organosilanes with organic halides used in organic chemistry to form carbon–carbon bonds (C-C bonds). ). This reaction was discovered in 1988 by Tamejiro Hiyama and Yasuo Hatanaka as a method to form carbon-carbon bonds synthetically with chemo- and regioselectivity
The coupling of 2-chlorobenzoic acid and aniline is illustrative: [4] C 6 H 5 NH 2 + ClC 6 H 4 CO 2 H + KOH → C 6 H 5 N(H)−C 6 H 4 CO 2 H + KCl + H 2 O. A typical catalyst is formed from copper(I) iodide and phenanthroline. The reaction is an alternative to the Buchwald–Hartwig amination reaction.
The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon-carbon bonds (C-C) in the process. A palladium (0) species is generally utilized as the catalyst, though nickel is sometimes used.
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Many Pd-catalyzed cross coupling reactions involve oxidative addition to form Pd(II) derivatives called oxidative addition complexes (OAC). The resulting L–Pd II (Ar)X OAC is electrophilic such that it reacts with a nucleophile and forms C–C and C–heteroatom bonds, after reductive elimination. [61] Such Pd II OACs have been used as ...