A new method for the fluorination of arylsulfur chlorotetrafluorides to arylsulfur pentafluorides is described. The reaction is promoted by hydrogen fluoride generated from potassium hydrogen fluoride and trifluoroacetic acid which also serves as a solvent. The reaction is performed under mild conditions and uses substochiometric amounts of potassium hydrogen fluorides in certain cases. Recovery and reuse of trifluoroacetic acid was successfully demonstrated which makes this method safe, simple to use, and atom- and cost-effective. (C) 2013 Elsevier B.V. All rights reserved.

ChemInformVolume 45, Issue 18 Isocyclic Compounds ChemInform Abstract: An Improved Method for the Fluorination of Arylsulfur Chlorotetrafluorides to Arylsulfur Pentafluorides. Katrin Lummer, Katrin Lummer Inst. Org. Chem., Acad. Sci. Czech Rep., CZ-166 10 Prague 6, Czech RepublicSearch for more papers by this authorMaxim V. Ponomarenko, Maxim V. Ponomarenko Inst. Org. Chem., Acad. Sci. Czech Rep., CZ-166 10 Prague 6, Czech RepublicSearch for more papers by this authorGerd-Volker Roeschenthaler, Gerd-Volker Roeschenthaler Inst. Org. Chem., Acad. Sci. Czech Rep., CZ-166 10 Prague 6, Czech RepublicSearch for more papers by this authorMatthias Bremer, Matthias Bremer Inst. Org. Chem., Acad. Sci. Czech Rep., CZ-166 10 Prague 6, Czech RepublicSearch for more papers by this authorPetr Beier, Petr Beier Inst. Org. Chem., Acad. Sci. Czech Rep., CZ-166 10 Prague 6, Czech RepublicSearch for more papers by this author Katrin Lummer, Katrin Lummer Inst. Org. Chem., Acad. Sci. Czech Rep., CZ-166 10 Prague 6, Czech RepublicSearch for more papers by this authorMaxim V. Ponomarenko, Maxim V. Ponomarenko Inst. Org. Chem., Acad. Sci. Czech Rep., CZ-166 10 Prague 6, Czech RepublicSearch for more papers by this authorGerd-Volker Roeschenthaler, Gerd-Volker Roeschenthaler Inst. Org. Chem., Acad. Sci. Czech Rep., CZ-166 10 Prague 6, Czech RepublicSearch for more papers by this authorMatthias Bremer, Matthias Bremer Inst. Org. Chem., Acad. Sci. Czech Rep., CZ-166 10 Prague 6, Czech RepublicSearch for more papers by this authorPetr Beier, Petr Beier Inst. Org. Chem., Acad. Sci. Czech Rep., CZ-166 10 Prague 6, Czech RepublicSearch for more papers by this author First published: 17 April 2014 https://doi.org/10.1002/chin.201418086Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume45, Issue18May 6, 2014 RelatedInformation

The synthesis of SF5- and CF3-substituted benzenes and naphthalenes from various 7-oxanorbornene derivatives utilizing SF5Cl and CF3I radical addition reactions, followed by dehydrohalogenation and aromatization, is reported. The differences in the behavior of the SF5- and CF3-containing intermediates under basic and acidic conditions are discussed. The experimentally observed high regioselectivities of the formation of 2-RF-substituted-1-naphthols agree well with the ab initio computations, revealing the first example of the SF5···HO hydrogen bonding.