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Aerobic Carbon-Carbon Bond Cleavage of Alkenes to Aldehydes and Ketones

Technology Number: 

1722

Principal Investigator

Prof.
Ronny
Neumann

Department: 

Organic Chemistry
Summary 

Our technology provides a new type of oxidative cleavage reaction of organic compounds with highly selective product formation.
Polyoxometalate (POM) catalysts have become well-known for their utility and diversity in specific reactions. Through the elucidation of POM catalytic pathways, greater versatility has been achieved. This technology is one such application of a novel POM catalyst and is exploited to cleave carbon-carbon double bonds in alkenes (olefins) through an aerobic oxidation reaction. Oxidation reactions are of particular interest because they are difficult to achieve on an industrial scale while maintaining “green” chemistry practices. [1]

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[1] Green Chem., 2007, 9, 717-730

Applications


  • As a novel catalyst in industrial organic chemistry processes
  • Sold as a stand-alone catalyst for laboratory or individual use

Advantages


  • Environmentally friendly oxidation reaction
  • Easy catalyst regeneration

Technology's Essence


Our approach is motivated by societal considerations that demand environmentally benign and sustainable solutions for oxidative reactions. As such, we have developed a scheme to react NO2 with a transition-metal-substituted POM which yields a metal-nitro intermediate that is competent for forming the precursors for oxidation with molecular oxygen, O2, to have a final product of ketones and/or aldehydes, and regenerate the POM catalysts.[1]
This method has preference towards di/tri-substituted alkenes. High yields of ketones or aldehydes have been produced and the POM catalyst is regenerated without further oxidation to carboxylic acids, as is typical with other oxidative catalysts.
The selective cleavage of carbon-carbon double or triple bonds with metal-nitro or metal-nitrito compound has not been reported. This exciting new discovery could lead to a wide variety of organic reactions not previously possible, along with revolutionary green oxidative chemistry techniques.

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[1] J. Am. Chem. Soc., 2014, 136(31), pp10941-10948 

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