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Fe-Catalyzed three-component carboazidation of alkenes with alkanes and trimethylsilyl azide

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Abstract

Reported herein is a novel iron-catalyzed, DTBP-mediated carboazidation of alkenes using cycloalkanes, CH2Cl2, CHCl3 and CCl4 as alkylating reagents to generate electrophilic or nucleophilic alkyl radicals. Mechanistic studies suggested that the reaction proceeded via the addition of alkyl radicals to alkenes followed by an iron-mediated ligand transfer process. The reaction is unique as it is applicable not only to diversely functionalized electron rich alkenes, but also to electron-poor olefins to provide chain extended azides and γ-azido chloroalkanes in good to high yields.

Graphical abstract: Fe-Catalyzed three-component carboazidation of alkenes with alkanes and trimethylsilyl azide

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Publication details

The article was received on 26 Jun 2018, accepted on 03 Sep 2018 and first published on 04 Sep 2018


Article type: Communication
DOI: 10.1039/C8CC05090B
Citation: Chem. Commun., 2018, Advance Article
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    Fe-Catalyzed three-component carboazidation of alkenes with alkanes and trimethylsilyl azide

    W. Li, C. Wu, Z. Wang and Y. Luo, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC05090B

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