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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.

SUBMITTER: Chen G

PROVIDER: S-EPMC5595123 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature

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

Chen Gui G Song Jinshuai J Yu Yinghua Y Luo Xuesong X Li Chunsen C Huang Xueliang X

Chemical science 20151214 3

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 <i>N</i>-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 v ...[more]

PMID: 28959390

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