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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 ?-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, ?-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.

SUBMITTER: Huang Z

PROVIDER: S-EPMC5126259 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature

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

Huang Zhongyan Z Okuyama Kenta K Wang Chen C Tokunaga Etsuko E Li Xiaorui X Shibata Norio N

ChemistryOpen 20160128 3

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, ...[more]

PMID: 27933224

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