Method for producing coupling compound

Details Method for producing coupling compound Method for producing coupling compound

2006-08-17

2009-06-30

Shiao, Rei-tsang (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C568S312000, C568S322000, C568S323000, C568S626000, C548S312400, C502S167000

Reexamination Certificate

active

07553988

ABSTRACT:
A method is provided for producing a specific crosscoupling compound and a specific catalyst for producing the compound. The method includes reacting in the presence of a base and a nickel compound catalyst organic halide of the formula n′(R1X1n), wherein R1is a hydrocarbon group and the α and β carbons to X′ are sp3carbon atoms; X1is a chlorine, bromine, or iodine atoms, and n and n1are 1 or 2 but not both 2, with a compound having the formula m{R2(BX22)n′} where an R2is an aryl, heteroaryl, or alkenyl group, and n′ is 1 or 2, X2is independently a hydroxyl group, an alkoxy or arylalkoxy group or X22together form an alkylenedioxy or arylenedioxy group, and m represents 1 or 2 but m≦n, and the boron atom is bonded to a sp2carbon atom of R2group or a boronic acid trimer anhydride.

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: 7238832 (2007-07-01), 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
patent: WO 01/66248 (2001-09-01), None
Netherton et al., “Suzuki Cross-Coupling of Alkyl Tosylates that Possess β Hydrogen Atoms: Synthetic and Mechanistic 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).
Elgafi et al., “Synthesis of novel ruthenium complexes containing bidentate imidazole-based ligands”,J. Chem Soc. Dalton Trans., pp. 2341-2345, (1997).
Satake, “Synthesis of Neutral π-Allylpalladium Complexes having Bisnitrogen Ligands and Palladium-Catalyzed Cyclopropanation of Ketene Silyl Acetates with Allylic Acetals”,Journal of Synthetic Organic Chemistry, vol. 58, No. 8, pp. 736-744, (2000).
Katalin OSZ3, “Copper(II), nickel(II) and zinc(II) complexes of amino acids containing bis(imidazol-2-yl)methyl residues”,Inorganica Chimica Acta, vol. 339, pp. 373-382, (2002).
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).
Duñach et al., “Carbon-Carbon Bond Formation with Electrogenerated Nickel and Palladium Complexes”,European Journal of Organic Chemistry, No. 9, pp. 1605-1622, (2003).

Affiliated with

Also associated with

Rating

Method for producing coupling compound does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method for producing coupling compound, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for producing coupling compound will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4091110