Palladium-catalyzed cross-coupling of aryldiazonium salts...

Chemistry of hydrocarbon compounds – Compound or reaction product mixture – Aromatic

Reexamination Certificate

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C585S024000, C585S026000, C585S027000, C585S454000, C585S469000, C585S470000, C585S471000

Reexamination Certificate

active

06838585

ABSTRACT:
A palladium catalyzed cross-coupling of aryldiazonium salts with organosilanes is disclosed. New reactions that are user friendly and environmentally friendly are now possible, including some reactions that could not be achieved using prior methods. The organosilanes that may be cross-coupled with aryldiazonium salts include, for example, Ar′—Si(L)3, where Ar′=aryl, and where L═CH3, OCH3, F, Cl, R, or OR.

REFERENCES:
Hatanaka, Y. et al., “Selective synthesis of unsymmetrical biaryls via palladium-catalyzed cross-coupling of arylfluorosilanes with aryl iodides,”Chem. Lett.1989, pp. 1711-1714, no month.
Hiyama, T., “Organosilicon compounds in cross-coupling reactions,” pp. 421-453 in F. Diederich et al. (Eds.),Metal-Catalyzed Cross-Coupling Reactions(Wiley-VCH Verlag 1998), no month.
Ikenaga, K. et al., “Reaction of diazonium salts with transition metals. Part 11. Palladium-catalyzed aryldesilylation of alkenylsilanes by arenediazonium salts,”J. Chem. Soc. Perkin Trans.1986, pp. 1959-1964.
Kikukawa, K. et al., “Reaction of diazonium salts with transition Metals. IX, Reaction of vinyltrimethylsilane with arenediazonium tetrafluoroborates under palladium(0) catalysis,”J. Organomet. Chem., vol. 270, pp. 277-282 (1984).
Spivak, D. and Simon, R., “Palladium catalyzed cross-coupling of silyl enol-ethers with arenediazonium salts,” Poster presented at Apr. 1-5, 2001 meeting of the American Chemical Society, San Diego, CA.
Spivak, D. and Simon, R., “Palladium catalyzed cross-coupling of silyl enol-ethers with arenediazonium salts,” Abstract of poster presented at Apr. 1-5, 2001 meeting of the American Chemical Society, San Diego, CA (abstract mailed to meeting participants approximately Feb. or Mar. 2001).

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