title: 2-Diazo-1-phenyl-2-((trifluoromethyl)sulfonyl)ethan-1-one: Another Utility for Electrophilic Trifluoromethylthiolation Reactions.
abstract: 2-Diazo-1-phenyl-2-((trifluoromethyl)sulfonyl)ethan-1-one (diazo-triflone) (2) is not only a building block but also a reagent. In this study, diazo-triflone, which was originally used for the synthesis of β-lactam triflones as a trifluoromethanesulfonyl (SO2CF3) building block under catalyst-free thermal conditions, is redisclosed as an effective electrophilic trifluoromethylthiolation reagent under copper catalysis. A broad set of enamines, indoles, β-keto esters, pyrroles, and anilines were nicely transformed into corresponding trifluoromethylthio (SCF3) compounds in good to high yields by diazo-triflone under copper catalysis via an electrophilic-type reaction. A coupling-type trifluoromethylthiolation reaction of aryl iodides was also realized by diazo-triflone in acceptable yields.
authors.affiliation: Department of Nanopharmaceutical Sciences Nagoya Institute of Technology Gokiso, Showa-ku Nagoya 466-8555 Japan.
authors.forename: Zhongyan
authors.initials: Z
authors.lastname: Huang
authors.affiliation: Department of Nanopharmaceutical Sciences Nagoya Institute of Technology Gokiso, Showa-ku Nagoya 466-8555 Japan.
authors.forename: Kenta
authors.initials: K
authors.lastname: Okuyama
authors.affiliation: Department of Nanopharmaceutical Sciences Nagoya Institute of Technology Gokiso, Showa-ku Nagoya 466-8555 Japan; Key Laboratory of Auxiliary Chemistry & Technology for Chemical Industry Ministry of Education Shaanxi University of Science & Technology Xi'an 710021 P. R. China.
authors.forename: Chen
authors.initials: C
authors.lastname: Wang
authors.affiliation: Department of Nanopharmaceutical Sciences Nagoya Institute of Technology Gokiso, Showa-ku Nagoya 466-8555 Japan.
authors.forename: Etsuko
authors.initials: E
authors.lastname: Tokunaga
authors.affiliation: Key Laboratory of Auxiliary Chemistry & Technology for Chemical Industry Ministry of Education Shaanxi University of Science & Technology Xi'an 710021 P. R. China.
authors.forename: Xiaorui
authors.initials: X
authors.lastname: Li
authors.affiliation: Department of Nanopharmaceutical Sciences Nagoya Institute of Technology Gokiso, Showa-ku Nagoya 466-8555 Japan.
authors.forename: Norio
authors.initials: N
authors.lastname: Shibata
keywords: carbines; fluorine; sulfur; triflones; trifluoromethylthiolation