2‐Diazo‐1‐phenyl‐2‐((trifluoromethyl)sulfonyl)ethan‐1‐one: Another Utility for Electrophilic Trifluoromethylthiolation Reactions. Issue 3 (28th January 2016)

• Record Type: Journal Article
• Authors: Huang, Zhongyan; Okuyama, Kenta; Wang, Chen; Tokunaga, Etsuko; Li, Xiaorui; Shibata, Norio
• Is Part Of: ChemistryOpen. Volume 5:Issue 3(2016:Jun.)
• Page Start: 188
• Page End: 191
• Publication Date: 2016-01-28
• Subjects: carbines -- fluorine -- sulfur -- triflones -- trifluoromethylthiolation; Chemistry -- Periodicals; 540; 540.5
• DOI: 10.1002/open.201500225
• Languages: English
• ISSNs: 2191-1363

Abstract

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 (SO2 CF3 ) 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. Abstract : Double‐sided utility ! 2‐Diazo‐1‐phenyl‐2‐((trifluoromethyl)sulfonyl)ethan‐1‐one (2 ), which was originally used for the synthesis of β‐lactam triflones as a SO2 CF3 building block under catalyst‐free thermal conditions, is redisclosed as an effective electrophilic SCF3 reagent under copper catalysis. Enamines, indoles, β‐keto esters, pyrroles, anilines, and aryl iodides were nicely transformed into corresponding SCF3 compounds by diazo‐triflone2 under copper catalysis.