By a News Reporter-Staff News Editor at Journal of Engineering -- From Alexandria, Virginia, VerticalNews journalists report that a patent by the inventors Saito, Norimichi (Yamaguchi, JP); Shibata, Norio (Aichi, JP); Matsuzaki, Kohei (Aichi, JP); Okuyama, Kenta (Aichi, JP), filed on August 13, 2015, was published online on June 28, 2016.
The patent's assignee for patent number 9376384 is UBE INDUSTRIES, LTD. (JP).
News editors obtained the following quote from the background information supplied by the inventors: "The pentafluorosulfanyl (SF.sub.5) group is known to exhibit a strong electron-withdrawing property due to the presence of fluorine atoms, and also to have high lipophilicity. Thus, compounds containing a SF.sub.5 group are expected to be applied to physiologically active substances such as liquid crystal materials and pharmaceutical and agricultural chemicals. However, a process for introducing a SF.sub.5 group into a compound of interest is not easy to carry out since this process uses chlorine gas or the like and so requires sophisticated equipment and skilled techniques. Thus, there has hitherto been reported a process for synthesizing a biaryl compound containing a SF.sub.5 group by subjecting an aromatic compound containing a SF.sub.5 group to coupling reaction in the presence of a transition metal catalyst (Non-patent Literature 1)."
As a supplement to the background information on this patent, VerticalNews correspondents also obtained the inventors' summary information for this patent: "Technical Problem
"However, there has been a need for a simpler process for introducing a SF.sub.5 group into a compound of interest. In particular, introducing a pentafluorosulfanyl-containing aryl (hereinafter also called 'ArSF.sub.5') group, in which a SF.sub.5 group is bonded to an aromatic ring, into a compound of interest, if possible, will be of great advantage in pharmaceutical and other fields. In view of these circumstances, the present invention has as its object to provide a compound that allows easy introduction of an ArSF.sub.5 group into a compound of interest.
"Solution to Problem
"The present inventors found that particular diaryliodonium salts can achieve the above-mentioned object, and thus completed the present invention. More specifically, the above-mentioned object is achieved by the present invention as described below. (1) A diaryliodonium salt of the general formula (d) shown below. (2) The diaryliodonium salt as set forth in (1), wherein m is 0 and n is 3. (3) The diaryliodonium salt as set forth in (2), wherein R.sup.2 is a methyl group, an ethyl group, a n-propyl group, or an i-propyl group. (4) The diaryliodonium salt as set forth in (1), wherein m is 0 and n is 0. (5) A process for preparing the diaryliodonium salt as set forth in any one of (1) to (4), the process comprising:
"providing a compound of the general formula (b) shown below; and
"subjecting said compound to an oxidation reaction and a Friedel-Crafts reaction with a compound of the general formula © shown below at the same time to produce the diaryliodonium salt of the general formula (d). (6) A process for preparing a compound of the general formula (f) shown below, the process comprising reacting a compound of the general formula (d) shown below with a nucleophilic compound Z to introduce an aryl group containing a pentafluorosulfanyl group into the nucleophilic compound. (7) The process as set forth in (6), wherein the nucleophilic compound Z is selected from the group consisting of a 1,3-dicarbonyl compound, a phenol compound, an aniline compound, a heterocyclic compound, an alcohol compound, an oxyimide compound, an aromatic sulfur compound, and an aromatic cyanogen compound.
"Advantageous Effects of Invention
"The present invention can provide a diaryliodonium salt which allows easy introduction of an ArSF.sub.5 group into a compound of interest."
For additional information on this patent, see: Saito, Norimichi; Shibata, Norio; Matsuzaki, Kohei; Okuyama, Kenta. Diaryliodonium Salt. U.S. Patent Number 9376384, filed August 13, 2015, and published online on June 28, 2016. Patent URL: http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G&l=50&s1=9376384.PN.&OS=PN/9376384RS=PN/9376384
Keywords for this news article include: UBE INDUSTRIES LTD.
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