Copper Catalyzed
Ullmann coupling reaction
Reactions in which iodoaromatics are coupled to themselves to obtain diaryl compounds catalyzed by Cu, Ni or Pd.
Goldberg coupling reaction
Arylation catalyzed by copper or copper salts. This reaction was first discovered by Irma Goldberg, a German chemist and wife of Fritz Ullmann. However, this reaction has some drawbacks: (1) the reaction temperature is generally 140°C or even higher; (2) part of the reaction requires one mole or more of copper to participate in the reaction; and (3) it generally needs to be carried out in highly polar and toxic solvents. In recent years, the use of copper has been scaled down to catalytic amounts using suitable ligands. The reaction does not require the use of the expensive Pd metal, which is economically advantageous.
Kinugasa β-lactam synthesis reaction
The reaction catalyzed by a chiral organocopper (chiral oxazolidine) catalyst in which a dipolar cycloaddition of the terminal alkynes and nitrone yields an isoxazolidine intermediate, which is rearranged to give a stereoselective β-lactam.
Meerwein arylation reaction
Feringa-Alexakis asymmetric Michael addition reaction
Reaction of asymmetric Michael addition of alkyl zinc to unsaturated carbonyl compounds or unsaturated ketoimines catalyzed by chiral binaphthyl ligands and Cu(II).
Darzens-Nenitzescu olefin acylation reaction
A Zn-Cu-catalyzed reaction in which an olefin acylation product is obtained by the reaction of an acyl chloride and an olefin. The reaction is analogous to the Friedel-Crafts reaction.
Barton-Pinhey arylation reaction
A reaction in which lead aryltriacetate is coupled with an NH-containing amine or aromatic ring. This reaction can be used as an
alternative reaction to the Chan-Lam reaction. In addition to nucleophilic amines or aromatic rings that can react, electron-rich aromatic rings can also be coupled.
Nickel-Catalyzed Classes
Kumada coupling reaction
The Kumada coupling reaction is a Pd- or Ni-catalyzed coupling reaction first discovered in 1972.The reaction is an economical coupling of Grignard reagents with alkyl, alkenyl, or aryl halogenates, with the disadvantage that not all halogenates can be coupled to organomagnesium compounds.An important industrial application of the Kumada coupling is the synthesis of styrenic derivatives, which is a low-cost method of synthesizing asymmetric reaction of biaryl compounds.
This reaction, unlike Negishi Coupling, can be reacted directly with Grignard reagents without first being converted to organozinc reagents.
Kumada (cross) coupling reaction (Kumada Coupling; Kumadacoupling), also known as Kumada-Corriu (cross) coupling reaction, Kumada-Tamao-Corriu Coupling (Kumada-Tamao-Corriu Cross Coupling). It is a nickel- or palladium-catalyzed cross-coupling reaction of an alkyl or aryl Grignard reagent with an aryl halogen, a vinyl halogen, an aryl trifluoromethanesulfonate, and so on.
Negishi cross-coupling reaction
Nickel or palladium catalyzed cross-coupling of organozinc reagents with various halogenated or sulfonated esters (aryl, alkenyl, alkynyl and acyl).
Reactivity is generally good, alkyl (sp3) zinc compounds can also be used, and functional group compatibility is good.
Alternatively, coupling reactions using organoaluminum or organozirconium are also known as root-shore coupling reactions.
