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SF5 and OSF5 as Newly Available Functional Groups for Drug Discovery

Overview:

"Processes for synthesizing organic molecules containing the SF5 or OSF5 groups have been developed. Terminal alkenes and alkynes, internal alkenes and alkynes and cycloalkenes are all candidates for reaction with SF5Br or SF5Cl to produce SF5 functionality. Further, processes for converting addition products to aromatic molecules are disclosed as well as other know-how for handling starting materials and conducting reactions. While most of the SF5–related patents are issued, our OSF5 IP has not yet published but can be discussed under NDA. In the past, use of SF5 functional groups has been limited to compounds which could be synthesized from substituted aromatic SF5 compounds mainly derived from pentafluorosulfanyl nitrobenzene (SF5 PhNO2). Therefore, it was not simple for organic chemists to incorporate the SF5 group into a full range of aliphatic, cycloaliphatic, and aromatic substrates for further functionalization in applications like pharmaceutical and agricultural compounds. Literature references for other non-aromatic references are limited, and in many cases, involved reactions measured in days as opposed to hours or minutes as in the case of this technology. Finally, the requisite precursor molecules, SF5Br (or SF5Cl), were extremely limited or in fact, not commercially available. Air Products has commercialized SF5Br (or SF5Cl) for such applications and assembled a patent estate for exploiting the use of such gases in functionalizing a variety of organic molecules. This IP results in molecule synthesis on a much faster timeframe than past pioneering efforts in this field. Additionally, many molecules were simply not able to be functionalized with the SF5 group due to reaction limitations; with the use of this IP, however, many traditionally impossible to functionalize groups may now be easily reacted to place the SF5 in position. This offered technology has allowed for the synthetic chemist to incorporate SF5 and OSF5 groups into the commercial toolbox for the first time for many starting materials

Benefits:

  • Ability to incorporate SF5 group into alkenes or cycloakenes, or alkynes for the first time for many starting materials
  • Greatly reduced reaction times vs. non-initiated processes
  • Ability to perform reactions in liquid media with high yields
  • Access to new SF5 functional materials as potential synthons for new drug discovery
  • Reduced byproduct formation
  • Ease of removal of HBr elimination product after SF5Br addition
  • More efficient utility of SF5Br or SF5Cl reagents
  • Ability to utilize Air Products and Chemicals facilities and IP to creat novel intermediates incorporating SF5 moiety to serve your markets

IP Table

Title

Priority Patent Docket No.

Synthesis of Pentafluorosulfuranyl Substituted Alkanes US 6,870,068
Synthesis of Pentafluorosulfuranyl Substituted Arylenes US 6,958,415
Sulfurpentafluoride Compounds and Methods for Making and Using Same US 6,479,645

Fluorination Chemistry and Processes Available for Licensing
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