Arylation of olefins

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

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Reexamination Certificate

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06858756

ABSTRACT:
The present invention relates to a process for the arylation of olefins by reaction of haloaromatics or arylsulfonates with olefins in the presence of a palladium catalyst, a bulky nitrogen base and a dipolar aprotic solvent.

REFERENCES:
patent: 3922299 (1975-11-01), Heck
patent: 4564479 (1986-01-01), Spencer
patent: 6291383 (2001-09-01), Zapf et al.
Portnoy et al, Organometallics, Reactions of Electron-Rich Arylpalladium Complexes with Olefins. Origin of the Chelate Effect in Vinylation Catalysis, 1994, 13, pp. 3465-3479.*
J. Am. Chem. Soc. (month unavailable) 2001, 123, pp. 6989-7000, Adam F. Littke and Gregory C. Fu, “A Versatile Catalyst for Heck Reactions of Aryl Chlorides and Aryl Bromides under Mild Conditions”.
Littke, A F et al: “A versatile catalyst for Heck reactions of aryl chlorides and aryl bromides Under mild conditions” Journal of the American Chemical Society., Bd. 123, Nr. 29, 2001, Seiten 6989-7000 XPOO2236859 American Chemical Society, Washington, DC., US ISSN: 002-7863 Seite 6991, Spalte 12, Zeile 30—Zeile 40 Tabellen 1-3.
Beller M et al: “First Efficient Palladium-Catalyzed Heck Reactions of Aryl Bromides with Alkyl Methacrylate” Tetrahedron Letters, Elsevier Science Publishers, Amsterdam, NL, Bd. 37, Nr. 36, Sep. 2, 1996, Seityen 6535-6538, XPOO4030736 ISSN: 0040-4039 Seite 6536 Beispiele 1 ,4-8; Tabelle 1.
Reetz M T et al: “A New Catalyst System for the Heck Reaction of Unreactive Aryle Halides” Angewandte Chemie. International Edition Verlag Chemie. Weinheim, DE, Bd. 37, Nr. 4, 1998, Seiten 481-483m XPOO2160618, ISSN: 5070-0833 das ganze Dokument.
Baek, G H et al: “Synthesis of 3-Arylpropylamine Derivatives from Aryl Halides Using Heck Reactions” Bulletin of the Korean Chemical Society, XX, XX, Bd. 20, Nr. 2, 1999, Seiten 232-236, XPOO1006391 Seite 232, Spalte 2, Absatz 2 Tab Ile 1.

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