Method for producing biaryl compound

Chemistry of hydrocarbon compounds – Aromatic compound synthesis – From nonhydrocarbon feed

Reexamination Certificate

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Reexamination Certificate

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07122711

ABSTRACT:
There is disclosed a method for producing a biaryl compound of formula (I):wherein R1is the same or different and independently denotes a substituted or unsubstituted hydrocarbon group or the like, A and B denote an aromatic hydrocarbon ring having from 6 to 14 carbon atoms or the like, k and m independently denote an integer of from 0 to 5, and l denotes an integer of 1 or 2, which method is characterized by reacting an aromatic compound of formula (II):wherein R1, k and l denote the same as defined above, and X1denotes a leaving group, with a Grignard reagent of formula (III):wherein R2, B, and m denote the same as defined above and X2denotes chlorine or the like, in the presence of a cyclic ether, or an acyclic ether having two or more ether oxygens in the molecule and a nickel catalyst.

REFERENCES:
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patent: 2 804 956 (2001-08-01), None
patent: 2000-229243 (2000-08-01), None
patent: WO 01/66248 (2001-09-01), None
T. Kamikawa et al., “Palladium Catalysts for Cross-Coupling of Ortho-Substituted Aryl Triflates with Grignard Reagents”,SYNLETT, Feb. 1997, pp. 163-164.
K. Tamao et al., “Nickel-Phosphine Complex-Catalyzed Grignard Coupling. I. Cross-Coupling of Alkyl, Aryl, and Alkenyl Gregnard Reagents with Aryl and Alkenyl Halides: General Scope and Limitations”,Bulletin of the Chemical Society of Japan, vol. 49, No. 7, 1976, pp. 1958-1969.
A. Satake, “Synthesis of Neutral π-Allylpalladium Complexes having Bisnitrogen Ligands and Palladium-Catalyzed Cyclopropanation of Ketene Silyl Acetals with Allylic Acetates”,Yukigosei kagakukyokai-sho, vol. 58, No. 8, 2000.
V. Böhm et al., “Nickel-Catalyzed Cross-Coupling of Aryl Chlorides with Aryl Grignard Reagents”,Angew. Chem. Int. Ed., vol. 39, No. 9, 2000, pp. 1602-1604.

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