Aminofluorination: Transition-metal-free N–F Bond Insertion into Diazocarbonyl Compounds
Author(s): Sudhir Kumar Mishra
Publication #: 2201002
Date of Publication: 07.01.2022
Country: India
Pages: 5-11
Published In: Volume 8 Issue 1 January-2022
DOI: https://doi.org/10.5281/zenodo.7514268
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.
Keywords: Diazoacetate, Carbenoid Intermediates, Difunctionalization, Carbene, Aminofluorination, Bronsed Acids, Benzenesulfonimide
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