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Regiospecific Oxiation of Carbon-metal Bonds of Organometallic Compounds

In yet another embodiment of the invention, a method is provided for the regiospecific catalytic oxidation of the carbon-palladium bond of cyclopalladated azo compounds using chiral iron(III) salen complex as the catalyst.
In still another embodiment of the invention, the catalyst is prepared of Iron(III) complexes with inexpensive and readily available substituted salen ligands. The chiral iron(III)-salen complexes used as catalysts is with electron withdrawing and electron-releasing substituents at salicylidene moiety,. The preferred catalyst is the iron(III)-salen complexes with electron-withdrawing substituents.
In still another embodiment of the invention, the oxidant for the regiospecific oxidation of the carbon-metal bond like carbon-palladium bond is inorganic or organic peroxides such as but not limited to hydroperoxides t-BuOOH , tert-alkyl hydroperoxide, cumene hydroperoxide, hydrogenperoxides. The preferred oxidant is hydrogen peroxide, it being environmetal friendly with the formation of no undesirable byproduct.
In another embodiment of the present invention, the solvent system used for the oxidation of the carbon-metal bond like carbon-palladium bond essentially includes acetonitrile; dichloromethane.
In yet another embodiment of the invention, the solvents acetonitrile; dichloromethane used for the oxidation of the carbon-metal bond does not interfere with the oxidation process hence does not produce any undesirable side products.
In still another embodiment of the invention, the time duration for oxygenation reaction of the carbon palladium bond with hydrogen peroxide as the oxidant, iron(III) salen complex as the catalyst and acetonitrile as the solvent system is 0.5hr.
In still another embodiment of the invention, the regiospecific catalytic oxidation method of the carbon-metal bond with iron(III)salen catalyst may have applications in the oxidation of several industrial and pharmaceutical compounds.
In yet another embodiment of the invention, the oxidation of the carbon –metal bond at an industrial scale with the present process will generate minimal waste stream.
Activation of C-H bonds that is catalyzed by transition metals has been an important area of intensive investigation for several decades. The transformation of a C-H to a C-M bond, selective oxidation of a C-M to a C-OM bond, and then reductive demetalation of this O-M bond finally leads to the functionalization of the C-H to a C-OH bond. In this three-step process, the reaction involving the oxidation of the C-M bond is very important, because it requires a specific reagent and reaction conditions so that other sites susceptible to oxidation remain unaffected. The C-M bond oxidation reactions have immense industrial significance if it achieves high yield
Different methods for the oxidation of palladium-carbon bonds by inorganic and organic peroxides are known. These methods suffer from the disadvantages as the total reaction times with those methods were 12-24 hrs. Oxidation of C-Pd bonds of the azo compounds with hydrogen peroxide using porphyrin catalyst in methanol dichloromethane solvent system are also given in the literature. However in this method at lower substrate concentration there was competitive oxidation of methanol with the production appreciable amount of formic acid along with the oxidized product.
The drawback in the prior art of regiospecific oxidation of C-Pd bond mainly refers to the undesirable side reaction and prolonged reaction time. The present invention proposes to overcome the drawback of the prior art methods by developing a process of regiospecific oxidation of C-Pd bond with hydrogen peroxide using inexpensive iron (III)-salen catalyst under mild reaction conditions. The solvent system used in this method never interferes in the oxidation reaction.

Sector: Biotechnology
Country: India
Area of Application:
The principal object of the present invention is to provide method for regiospecific catalytic oxidation of the carbonmetal bond of the organometallic compounds. Yet another object of the present invention is to provide a method for regiospecific catalytic oxidation of the caarbonmetal bond with no undesirable side reactions. Yet another object of the invention is to reduce the reaction time of the oxygenation of the carbon-metal bond. Still another object of the present invention is the use of the low cost metallosalen complexes as the catalyst for the catalytic oxygenation of the carbon-metal bond. Another object of the invention is the use of solvent system that will not produce undesirable byproduct through competitive oxidation. Yet another object of the invention is the use of low cost and biofriendly oxidant for the oxygenation of the carbon-metal bond. Still another object of the invention is to provide a method with mild reaction conditions for the oxygenation of the carbon-metal bond. Another object of the invention is to provide a catalytic oxidation method of metal-carbon bond which may be used in the oxidation of industriala and pharmaceutical compounds with multiple functionalities.
Keywords: cyclopalladated, dichloromethane, acetonitrile, spectrophotometrically
Advantages:
Environmental aspects: Environment friendly
Development Status: LaboratoryModel
Legal Protection: Patent
Technical specifications:
Transfer Terms:
  • Consultancy
  • Technical services
  • Technology Licensing
Target Countries:
  • Chile
  • China
  • India
  • New Zealand
  • Sri Lanka
  • United States of America (the)
  • United Kingdom
Estimated cost (US$):
Your Contact Details:
Contact Person: NA
Address: Amity University Uttar Pradesh
Sector-125, Noida
City: Distt Gautam Buddha Nagar
Country: India
Zip/Pin Code: 201303

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