Search results
Results from the WOW.Com Content Network
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:
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 . [ 1 ]
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.
Figure 1. Mechanism for a generic cross-coupling reaction with A) homogenous Pd in the presence of a ligand and B) heterogeneous, ligandless Pd as the Pd source. The role of the solid phase in heterogeneous metal catalyzed cross-coupling, then, is more subtle than one might expect.
Some of the cross-coupling reactions that include a transmetalation step are Stille cross-coupling, Suzuki cross-coupling, Sonogashira cross-coupling, and Negishi cross-coupling. The most useful cross-coupling catalysts tend to be ones that contain palladium. Cross-coupling reactions have the general form of R′–X + M–R → R′–R + M ...
[citation needed] The example of a coupling reaction reaction used in their preparation is an alternative to the traditional Suzuki and Stille cross-coupling reactions, and various catalysts have been employed for this transformation; Goossen et al. reported the formation of biaryls from palladium and copper-catalzyed cross-coupling reactions ...
The first example of a palladium catalyzed coupling of aryl halides with organotin reagents was reported by Colin Eaborn in 1976. [16] This reaction yielded from 7% to 53% of diaryl product. This process was expanded to the coupling of acyl chlorides with alkyl-tin reagents in 1977 by Toshihiko Migita, yielding 53% to 87% ketone product. [17]