Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
2007-07-03
2007-07-03
Witherspoon, Sikarl A. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C568S312000, C568S322000, C568S323000, C568S626000, C570S144000, C558S411000
Reexamination Certificate
active
10781198
ABSTRACT:
There is provided a method for producing a coupling compound of formula (1):in-line-formulae description="In-line Formulae" end="lead"?(Y—)(n−1)R1—R2—(R1)(n′−1) (1)in-line-formulae description="In-line Formulae" end="tail"?wherein R1, R2n and n′ are as defined below, Y is R2or X as defined below, which method comprises reacting an organic halogen compound of formula (2):in-line-formulae description="In-line Formulae" end="lead"?n′(R1X1n) (2)in-line-formulae description="In-line Formulae" end="tail"?wherein X1represents a bromine or iodine, R1represents a substituted or unsubstituted, linear, branched or cyclic hydrocarbon group of which α and β carbon atoms in relation to X1are sp3 carbon atoms, n and n′ each independently represent an integer of 1 or 2, and provided that n and n′ do not simultaneously represent 2, with an organic boron compound of formula (3):in-line-formulae description="In-line Formulae" end="lead"?m{R2(BX22)n′} (3)in-line-formulae description="In-line Formulae" end="tail"?wherein R2represents a substituted or unsubstituted aryl group or a substituted or unsubstituted alkenyl group and the boron atom is bonded with a sp2 carbon atom thereof, X2represents a hydroxyl or alkoxy group, n′ is as defined above, m represents an integer of 1 or 2, and m is not more than n, in the presence of a catalyst comprising a) a nickel compound, andb) b-1) a compound of formula (i):orb-2) a compound of formula (ii):
REFERENCES:
patent: 5922898 (1999-07-01), Miller et al.
patent: 6194599 (2001-02-01), Miller et al.
patent: 6395916 (2002-05-01), Buchwald et al.
patent: 7041856 (2006-05-01), Itahashi et al.
patent: 2002/0016489 (2002-02-01), Marcuccio et al.
patent: 2003/0158419 (2003-08-01), Kamikawa et al.
patent: 2003/0162950 (2003-08-01), Itahashi et al.
patent: 152 547 (1981-12-01), None
patent: 0 366 573 (1990-05-01), None
patent: WO 00/68252 (2000-11-01), None
Akiharu Satake, “Synthesis of Neutral π-Allylpalladium Complexes having Bisnitrogen Ligands and Palladium-Catalyzed Cyclopropanation of Ketene Silyl Acetals with Allylic Acetates”, Yukigosei Kagaku Kyokai-Shi, vol. 58, No. 8, pp. 736-744, (2000).
M.R. Netherton et al., “Suzuki Cross-Couplings of Alkyl Tosylates that Process β Hydrogen Atoms: Synthetic Studies”, Angew. Chem. Int. Ed., vol. 41, No. 20, pp. 3910-3912, (2002).
Leadbeater et al., “Suzuki Aryl Couplings Mediated By Phosphine-Free Nickel Complexes”, Tetrahedron, vol. 55, pp. 11889-11894, (1999).
Kirichhoff et al., “Boronic Acids: New Coupling Partners in Room-Temperature Suzuki Reactions of Alkyl Bromides. Crystallographic Characterization Of An Oxidative-Addition Adduct Generated under Remarkably Mild Conditions”,Journal of American Chemical Society, vol. 124, No. 46, pp. 13662-13663, (2002).
Dunach et al., “Carbon-Carbon Bond Formation with Electrogenerated Nickel and Palladium Complexes”,European Journal of Organic Chemistry, No. 9, pp. 1605-1622, (2003).
Itahashi Tamon
Kamikawa Takashi
Akin Gump Strauss Hauer & Feld & LLP
Sumitomo Chemical Company Limited
Witherspoon Sikarl A.
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