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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:
A 2021 survey of heterogeneous metal catalyzed cross-couplings in the fine chemical industry reported, out of 22 examples, 19 Suzuki or Heck reactions, which included only 2 examples with N-basic heterocycles, and only 4 examples with a singly-ortho-substituted electrophile (representative example in Scheme 1). [1]
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: Homocouplings joining two ...
This reaction is notable for using organolithiums as opposed to other cross-coupling reactions which utilize various metal-carbon compounds (metal = tin, magnesium, boron, silicon, zinc). Since the production of these other coupling reagents relies heavily upon organolithiums (especially in the case of organozinc and organomagnesium compounds ...
The Liebeskind–Srogl coupling reaction is an organic reaction forming a new carbon–carbon bond from a thioester and a boronic acid using a metal catalyst. It is a cross-coupling reaction. [1] This reaction was invented by and named after Jiri Srogl from the Academy of Sciences, Czech Republic, and Lanny S. Liebeskind from Emory University ...
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–X and are used to form C–C bonds. R and R′ can be any carbon fragment. The identity of the metal, M, depends on which cross-coupling reaction is being used. Stille reactions ...
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.
The first example of organogermanes used in transition-metal-catalyzed cross-coupling reaction was reported in 2004. [1] However, due to the toxicity, low reactivity (compared with other Ar–[M] nucleophiles) and poor stability of ArGeCl 3, this reaction was demonstrated not to be synthetically applicable.