Method for producing diphosphines and the use thereof

Details Method for producing diphosphines and the use thereof Method for producing diphosphines and the use thereof

2005-08-02

2005-08-02

Richter, Johann (Department: 1621)

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

Organic compounds

Phosphorus acids or salts thereof

C564S015000, C568S017000, C568S014000

Reexamination Certificate

active

06924389

ABSTRACT:
Diphosphine of formula Iin-line-formulae description="In-line Formulae" end="lead"?R1R2P—H2C—Ar—CH2PR1R2  (I)in-line-formulae description="In-line Formulae" end="tail"?are prepared by a process that comprises a) reacting a dimethyl compound of formula IIin-line-formulae description="In-line Formulae" end="lead"?H3C—Ar—CH3  (II)in-line-formulae description="In-line Formulae" end="tail"?with a base and an N-substituted aminophosphorous halide to form bis(aminophosphinomethyl) compound of the formula IIIin-line-formulae description="In-line Formulae" end="lead"?R3R4P—H2C—Ar—CH2—PR3R4  (III)in-line-formulae description="In-line Formulae" end="tail"?b) reacting the compound of formula III with HCl to form bis(dichlorophosphinomethyl) compound of formula IVin-line-formulae description="In-line Formulae" end="lead"?Cl2P—H2C—Ar—CH2—PCl2  (IV)in-line-formulae description="In-line Formulae" end="tail"?and c) reacting the compound of formula IV with an organometallic reagent to give the product compound of formula I, wherein groups R1and R2are each, independently of one another, a substituted or unsubstituted aromatic, heteroaromatic or aliphatic hydrocarbon group and may have a covalent bond connecting them and Ar is a substituted or unsubstituted aromatic or heteroaromatic hydrocarbon group an R3and R4are each, independently of one another, an N-substituted alkylamino or arylamino group.

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Evleth E M et al: “p-Phenylenediphosphine and Related Compounds” Journal of Organic Chemistry, American Chemical Society, vol. 27, pp. 2192-2197, 1962.
Marinetti A et al: “New Chiral Dichlorophosphines and Their Use in the Synthesis of Phosphetane Oxides and Phosphinic Chlorides” Journal of Organic Chemistry, American Chemical Society, vol. 62, No. 2, pp. 297-301, Jan. 24, 1997.
Reetz M T et al: “New non-C2-symmetric phosphine-phosphonites as ligands in asymmetric metal catalysis” Tetrahedon: Asymmetry, vol. 10, No. 11, pp. 2129-2137 Jun. 4, 1999.
Van Doorn J A et al: “Reductive cleavage of the carbon-phosphorus bond with alkali metals. III Reactions of arylalkylphosphines” Recueil des Travaux Chimiques des Pays-Bas, vol. 111, No. 4, pp. 170-177, 1992.
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Gillie A et al: “Mechanisms of 1, 1-Reductive Elimination from Palladium” Journal of the American Chemical Society, vol. 102, No. 15, 1980, pp. 4933-4941, XP002203113 the whole document.
Dani P et al: “Replacement of a Cyclometalated Terdentate Diamino Ligand by a Phosphorus Analogue. Isolation and Crystallographic Characterisation of an Intermediate in Aryl C-H Bond Activation in Models of Dendrimer-Bound Organometallic Catalysts” Journal of the American Chemical Society, vol. 119, No. 46, 1997, pp. 11317-11318, XP00203114 the whole document.
Yamamoto Y et al: “Preparation and characterization of palladium platinum complexes bearing 1,8-bis (diphenylphosphino) methyl!naphtalene” Journal of the Chemical Society, Dalton Transactions, 2001, pp. 1773-1781, XP002203115 the whole document.
Goertz W et al: “Asymetric Nickel-Catalyzed Hydrocyanation of Vinylarenes by Applying Homochiral Xantphos Ligands” Chemistry, A European Journal, vol. 7, No. 8, 2001, pp. 1614-1618, XP002203116 Seite 1617, Synthese der Verbindung 1.
Goertz W et al: “Electronic effects in the nickel-catalysed hydrocyanation of styrene applying chelating phosphorous ligands with large bite angles” Journal of the Chemical Society, Dalton Transactions, 1998, pp. 2981-2988, XP002195283 Seite 2986, Herstellung des Ligands L2a.
Bentrude W G et al: “Free-radical chemistry of organophosphorus compound. IV. Polar, bond strength and resonance effects of phosphoranyl radical formation” Journal of the American Chemical Society, vol. 95, No. 11, May 30, 1973, pp. 3625-3635, XP002203117 p. 3634, col. 1, line 19-line 24.
Evleth E M et al: “P-Phenylenediphosphine and Related Compounds” Journal of Organic Chemistry, American Chemical Society, Easton, US, vol. 27, Jun. 1962, pp. 2192-2197, XP001021629 ISSN:0022-3263 Seite 2192, Reaktionsschema.
Marinetti A et al: “New Chiral Dichlorophosphines and Their Use in the Synthesis of Phosphetane Oxides and Phosphinic Chlorides” Journal of Organic Chemistry, American Chemical Society. Easton, US, vol. 62, No. 2, Jan 24, 1997, pp. 297-301, XP000640625 ISSN: 0022-3263 Seite300, Synthese von 5a.
Reetz M T et al: “New non-C2-symmetric phosphine-phosphonites as ligands in asymmetric metal catalysis” Tetrahedon: Asymmetry, vol. 10, No. 11, Jun. 4, 1999, pp. 2129-2137, XP004174097 ISSN: 0957-4166 Seite 2130, Schema 1; Seite 2134, Teil 4.5.
Van Doorn J A et al: “Reductive cleavage of the carbon-phosphorus bond with alkali metals. III Reactions of arylalkylphosphines” Recueil des Travaux Chimiques des Pays-Bas, vol. 111, No. 4, 1992, pp. 170-177, XP001084949 Seite 175, rechte, Spaite, 1. Absatz des Experimental.

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