Process for producing phosphonium borate compound, novel...

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

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C423S299000, C423S276000

Reexamination Certificate

active

07728176

ABSTRACT:
The invention relates to a phosphonium borate compound represented by Formula (I) (hereinafter, the compound (I)). The invention has objects of providing (A) a novel process whereby the compound is produced safely on an industrial scale, by simple reaction operations and in a high yield; (B) a novel compound that is easily handled; and (C) novel use as catalyst.in-line-formulae description="In-line Formulae" end="lead"?Formula (I): (R1)(R2)(R3)PH.BAr4  (I)in-line-formulae description="In-line Formulae" end="tail"?wherein R1, R2, R3and Ar are as defined in the specification. The process (A) includes reacting a phosphine with a) HCl or b) H2SO4to produce a) a hydrochloride or b) a sulfate; and reacting the salt with a tetraarylborate compound. The compound (B) has for example a secondary or tertiary alkyl group as R1and is easily handled in air without special attention. The use (C) is characterized in that the compound (I) is used instead of an unstable phosphine compound of a transition metal complex catalyst for catalyzing C—C bond, C—N bond and C—O bond forming reactions and the compound produces an effect that is equal to that achieved by the transition metal complex catalyst.

REFERENCES:
patent: 7294600 (2007-11-01), Lee et al.
patent: 62-149721 (1987-07-01), None
patent: 62149721 (1987-07-01), None
patent: 2006004376 (2006-01-01), None
patent: 2006031067 (2006-03-01), None
Gusev et al., Synthesis, Structural Diversity, Dynamics, and Acidity of the M(II) and M(IV) Complexes [MH3(PR3)4]+ (M = Fe, Ru, Os; R = Me, Et, Journal of the American Chemical Society (1997), 119(16), 3716-3731 (Abstract).
Gill et al., {Transition metal-carbon bonds. XXXIII. Internal metalations of secondary and tertiary carbon atoms by platinum(II) and palladium(II) Inorganic Chemistry (1972-1999) (1973), (3), 270-278}.
Smith et al., {Phosphorus mustards. 1-3 III. Bis(2-chloroethyl)methylphosphine oxide and bis(2-benzoxyethyl)methylphosphine, Journal of Medicinal Chemistry, 11(5), 1060-3}.
Ayllon et al., {Proton Transfer I-3 in Aminocyclopentadienyl Ruthenium Hydride Complexes, Organometallics , 18(20), 3981-3990}.
Littke, Adam F.; Dai, Chaoyang; and Fu, Gregory C., “Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions”,Journal of American Chemical Society, 2000, 122, pp. 4020-4028.
Kirchhoff, Jan H.; Netherton, Matthew R.; Hills, Ivory D.; and Fu, Gregory C., “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, 2002, pp. 13662-13663, vol. 124, No. 46.
Jia, Guochen; and Morris, Robert H., “Wide Range of PKaValues of Coordinated Dihydrogen. Synthesis and Properties of Some η2-Dihydrogen and Dihydride Complexes of Ruthenium”,Journal of American Chemical Soceity, 1991, pp. 875-883, vol. 113, No. 3.
Netherton, Matthew R.; and Fu, Gregory C., “Air-Stable Trialkylphosphonium Salts: Simple, Practical, and Versatile Replacements for Air-Sensitive Trialkylphosphines. Applications in Stoichiometric and Catalytic Processes”,Organic Letters, 2001. pp. 4295-4298, vol. 3, No. 26.
Ayllon, José A.; Sayers, Stephen F.; Sabo-Etienne, Sylviane; Donnadieu, Bruno; and Chaudret, Bruno, “Proton Transfer in Aminocyclopentadienyl Ruthenium Hydride Complexes”,Organometallics, 1999, pp. 3981-3990, vol. 18, No. 20.
Gusev, Dmitry G.; Hübener, Rainer; Burger, Peter; Orama, Olli; and Berke, Heinz; Synthesis, Structural Diversity, Dynamics, and Acidity of the M(II) and M(IV) Complexes.[MH3(PR3)4]+(M = Fe, Ru, Os; R = Me, Et),Journal of American Chemical Society, 1997, vol. 119, No. 16, pp. 3716-3731.
Gill, D.F.; Mann, B.E.; and Shaw, B.L., “Transition Metal—Carbon Bonds. Part XXXIII. Internal Metallations of Secondary and Tertiary Carbon Atoms by Platinum(II) and Palladium(II)”,Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry, 1973, No. 3, pp. 270-278.
Cappellani, E. Paul; Drouin, Samantha D.; Jia, Guochen; Maltby, Patricia A.; Morris, Robert H.; and Schweitzer, Caroline T., “Effect of the Ligand and Metal on the pKaValues of the Dihydrogen Ligand in the Series of Complexes [M(H2)H(L)2]+, M = Fe, Ru, Os, Containing Isosteric Ditertiaryphospine Ligands, L”,Journal American Chemical Society, 1994, 116, pp. 3375-3388.
Patent Abstracts of Japan, Publication No. JP 62-149721, dated Mar. 7, 1987, “Epoxy Resin Composition for Sealing Semiconductor”, applicant: Hitachi Chem. Co., Ltd.; Inventors: Keiichi Kinashi et al.
Netherton, Matthew R.; and Fu, Gregory C., “Air-Stable Trialkylphosphonium Salts: Simple, Practical, and Versatile Replacements for Air-Sensitive Trialkylphosphines. Applications in Stoichiometric and Catalytic Processes”, Organic Letters, 2001, pp. 4295-4298, vol. 3, No. 26, Nov. 2003.
Smith et al. “Phosphorus Mustards. III. Bis(2-chloroethyl)methylphosphine Oxide and Bis(2-benzoxyethyl) methylphosphine”, Journal of Medicine Chemistry, vol. 11 No. 5, pp. 1060-1063, Sep. 1968.
Tan et al. “ Intermolecular Coupling of Alkenes to Heterocycles via C-H Bond Activation”, Journal of Organic Chemistry, vol. 69 No. 21, pp. 7329-7335, 2004.
Tan et al. “Microwave-Assisted C-H Bond Activation: A Rapid Entry Into Functionalized Heterocycles”, Organic Letters, vol. 5 No. 12, pp. 2131-2134, 2003.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Process for producing phosphonium borate compound, novel... does not yet have a rating. At this time, there are no reviews or comments for this patent.

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

Rate now

     

Profile ID: LFUS-PAI-O-4157536

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.