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ChemistryOpen. 2016 Jan 28;5(3):188-191. eCollection 2016 Jun.

2-Diazo-1-phenyl-2-((trifluoromethyl)sulfonyl)ethan-1-one: Another Utility for Electrophilic Trifluoromethylthiolation Reactions.

Author information

1
Department of Nanopharmaceutical Sciences Nagoya Institute of Technology Gokiso, Showa-ku Nagoya 466-8555 Japan.
2
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.
3
Key Laboratory of Auxiliary Chemistry & Technology for Chemical Industry Ministry of Education Shaanxi University of Science & Technology Xi'an 710021 P. R. China.

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.

KEYWORDS:

carbines; fluorine; sulfur; triflones; trifluoromethylthiolation

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