Reaktionsgleichung
[C:1]1([Mg]I)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2I)[CH:13]=[CH:12][CH:11]=1>C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Ni+2]>[C:1]1([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Nickel(II) acetylacetonate has affected other cross-coupling reactions, however. Mitchell and Yan, Can. J. Chem., 58, 2584 (1980), reported yields of 35-60%, 3,3"-dichloro-2,2"-dimethyl-o-terphenyl in the cross-coupling of 3-chloro-2-methylphenylmagnesium chloride with o-dibromobenzene in tetrahydrofuran using equivalent amounts of the reactants and 6 mole percent nickel(II) acetylacetonate based on the Grignard reagent. Ibuki, et al., Bull. Chem. Soc. Japan, 53, 821 (1980), reported cross-coupling two-fold excess phenylmagnesium bromide with 2-iodobiphenyl in the presence of 1.0% nickel(II) acetylacetonate based on the limiting reagent, obtaining a 78-80% yield of o-terphenyl. Clough, et al., J. Org. Chem., 41, 2256 (1976), reported cross-coupling an eight-fold excess of phenylmagnesium iodide with 1,8-diiodonaphthalene using 0.9 mole percent nickel(II) acetylacetonate based on the limiting reagent, producing 1,8-diphenylnaphthalene in 70% yield, while Corriu and Masse, J. Chem. Soc. Chem. Comm., 144 (1972), reported yields of 40 to more than 80% in cross-coupling reactions utilizing 0.1-1 percent nickel(II) acetylacetonate with respect to Grignard reagent.
Quellen und Nachweise
- ORD-Eintrag
- ord-65f77dab98f44caf8c7f3029ed21d0e5
- Quelldatensatz
- uspto-grants-1985_03
- Patentnummer
- US04507513
Verknüpfte Notizen
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