Issue 3, 2016

Aminofluorination: transition-metal-free N–F bond insertion into diazocarbonyl compounds

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.

Graphical abstract: Aminofluorination: transition-metal-free N–F bond insertion into diazocarbonyl compounds

Supplementary files

Article information

Article type
Edge Article
Submitted
07 Nov. 2015
Accepted
14 Dec. 2015
First published
14 Dec. 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2016,7, 1786-1790

Aminofluorination: transition-metal-free N–F bond insertion into diazocarbonyl compounds

G. Chen, J. Song, Y. Yu, X. Luo, C. Li and X. Huang, Chem. Sci., 2016, 7, 1786 DOI: 10.1039/C5SC04237B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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