Aminofluorination: transition-metal-free N–F bond insertion into diazocarbonyl compounds. Issue 3 (4th January 2016)

• Record Type: Journal Article
• Authors: Chen, Gui; Song, Jinshuai; Yu, Yinghua; Luo, Xuesong; Li, Chunsen; Huang, Xueliang
• Is Part Of: Chemical science. Volume 7:Issue 3(2016:Mar.)
• Page Start: 1786
• Page End: 1790
• Publication Date: 2016-01-04
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c5sc04237b
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Gem-aminofluorination of diazocarbonyl compounds has been achieved for the first time. Abstract : Gem-aminofluorination of diazocarbonyl compounds has been achieved for the first time. This reaction proceeds under mild conditions and does not require any transition-metal promoter or catalyst. Treatment of diazoesters with N -fluorobenzenesulfonimide (NFSI), which serves as both a fluorine and nitrogen source, results in the facile construction of C–N and C–F bonds, providing aminofluorination products in moderate to excellent yields. Kinetic studies and DFT calculations have provided valuable insight into the potential mechanism for this novel N–F bond insertion.