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Fluorination Agents

Overview:

Air Products is offering for license patents that relate to novel N,N’-difluorinated diazabicycloalkane derivatives and N-fluoro perfluoroheterocyclic sulfonamides, the processes for creating such compounds, and methods of using such compounds as fluorinating agents. The invention of the fluorinated diazabicycloalkane derivatives relates to the discovery that if an adduct with a readily fluorinatable moiety is formed at one or both nitrogen atoms of 1,4-diazabicyclo[2.2.2]octane, the resultant product can readily be fluorinated at one or both nitrogen atoms to provide effective electrophilic fluorinating agents. Mono- or di-adducts of other 1,4-diazabicycloalkanes can similarly be fluorinated to provide electrophilic fluorinating agents. According to the inventions the electrophilic fluorinating agents can be created by fluorinating the corresponding salts of the sulfonamide and diazoniabicycloalkane derivatives in the presence of an alkali metal salt. The fluorinations can be carried out using a stirred-tank batch reactor into which the fluorine is admitted either as a single charge of the gas at sub-atmospheric pressure or as a continuous flow of fluorine blended with nitrogen or other inert diluents at about atmospheric pressure. In industry, a demand currently exists for fluorinating agents which are site-selective toward organic, particularly carbanionic, substrates, especially for use in the preparation of pharmacologically active compounds. A number of such electrophilic fluorinating agents are known. These agents exhibited some problematic characteristics which make them unpractical in use unlike the agent created via this process.

Benefits:

  • Relatively inexpensive
  • Agent is not hazardous
  • Agent is convenient to handle
  • Agent is stable
  • Agent allows for site-selective fluorination of organic compounds
  • Readily obtainable from presently commercially available starting materials

IP Table

Title

Priority Patent Docket No.

Fluorinated Sulfonamide Derivatives US 5,227,493
Fluorinated Diazabicylcoalkane Derivatives US 5,473,065
Process for Preparing Difluorinated Diazoniabicycloalkane Derivatives US 5,367 071

Availability:

These patents are available for license on a worldwide basis. There are currently no exclusions for field of use.

Fluorination Agents
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