The 2,4-dimethyl-7-pentafluorosulfanyl-5-(trifluoromethyl)dibenzo[b,d]thiophenium trifluoromethanesulfonate: The SF5-analog of Umemoto salt

• Published in: Journal of fluorine chemistry Vol. 165; pp. 91 - 95
• Main Authors: Okazaki, Takao, Laali, Kenneth K., Reddy, A. Srinivas
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.09.2014; Elsevier
• Subjects: 4-(Pentafluorosulfanyl)benzenediazonium tetrafluoroborate; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Dibenzothiophenium; Physical Sciences; Science & Technology; SF5-biaryl; SF5-derivative; Trifluoromethylation of arenes; Umemoto salt; Trifluoromethylation of arenes; Dibenzothiophenium; SF5-biaryl; Umemoto salt; SF5-derivative; 4-(Pentafluorosulfanyl)benzenediazonium tetrafluoroborate; CATALYZED TRIFLUOROMETHYLATION; ELECTROPHILIC TRIFLUOROMETHYLATION
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2014.06.021

•The SF5-analog of Umemoto salt was prepared in just two steps.•The methodology illustrates the potential utility of 4-(pentafluorosulfanyl)benzenediazonium tetrafluoroborate as building block for SF5-aromatics.•Trifluoromethylating ability of the SF5-derivative of Umemoto salt toward reactive aromatics was surveyed. The SF5-analog of the Umemoto salt was synthesized in just two steps by combining our recently reported SF5-biaryl synthesis, via Suzuki coupling with 4-(pentafluorosulfanyl)benzenediazonium tetrafluoroborate, with Magnier's one-pot synthesis of dibenzothiophenium salts employing CF3SO2Na and triflic anhydride. The trifluoromethylating power of this novel onium salt toward reactive arenes was tested in a survey study on small scale.