Meerwein arylation reaction

The arylation of alkenes by treatment with a diazonium chloride (or bromide) solution and cupric chloride (or bromide) is called the Meerwein arylation reaction, after its discoverer (Meerwein et al., 1939). Originally, it was discovered using a,P-unsaturated carbonyl compounds, namely coumarin (Scheme 10-43) and cinnamic derivatives (Schemes 10-44 and 10-45). As Scheme 10-45 shows, the Meerwein reac-... 

Alkenes activated by an electron-withdrawing group (Z may be C=C, halogen, C=0, Ar, CN, etc.) can be arylated by treatment with a diazonium salt and a cupric chloride catalyst. This is called the Meerwein arylation reaction Addition of... 

Meerwein Arylation Reactions. Aryl diazonium ions can also be used to form certain types of carbon-carbon bonds. The copper-catalyzed reaction of diazonium ions with conjugated alkenes results in arylation of the alkene, known as the Meerwein arylation reaction.114 The reaction sequence is initiated by reduction of the diazonium ion by Cu(I). The aryl radical adds to the alkene to give a new (3-aryl radical. The final step is a ligand transfer that takes place in the copper coordination sphere. An alternative course is oxidation-deprotonation, which gives a styrene derivative. 

Mannich reaction, 1, 10 7, 3 Meerwein arylation reaction, 11, 3 24, 3 Meerwein-Ponndorf-Verley reduction, 2, 5 Mercury hydride method to prepare radicals, 48, 2... 

C. S. Rondestvedt, Jr., Arylation of unsaturated compounds by diazonium salts (the Meerwein arylation reaction), Org. React. 1976, 24, 225-259. 

Weis, C. D. Meerwein arylation reactions of olefins with anthraquinone diazonium hydrogen sulfates formation of new carbon bonds at the carbon atoms C-1 and at C-1,5 of the anthraquinone system. Dyes Pigm. 1988, 9, 1-20. 

Doyle, M. P., Siegfried, B., Elliott, R. C., Dellaria, J. F., Jr. Alkyl nitrite-metal halide deamination reactions. 3. Arylation of olefinic compounds in the deamination of arylamines by alkyl nitrites and copper(ll) halides. A convenient and effective variation of the Meerwein arylation reaction. J. Org. Chem. 1977, 42, 2431-2436. 

Arylation of Unsaturated Compounds by Diazonium Salts (The Meerwein Arylation Reaction) Christian S. Rondeslvedt, Jr. 

The reaction gives better yields with dienes, styrenes, or alkenes substituted with electron-withdrawing groups than with simple alkenes. These groups increase the rate of capture of the aryl radical. The standard conditions for the Meerwein arylation reaction employ aqueous solutions of diazonium ions prepared in the usual way. Conditions for in situ diazotization by t-butyl nitrite in the presence of CUCI2 and acrylonitrile or styrene are also effective. ... 

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