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Aminoxyl-Catalyzed Electrochemical Diazidation of Alkenes Mediated by a Metastable Charge-Transfer Complex

Juno C. Siu, Joseph B. Parry, Song Lin*

*Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States, Email: songlincornell.edu

J. C. Siu, J. B. Parry, S. Lin, J. Am. Chem. Soc., 2019, 141, 2825-2831.

DOI: 10.1021/jacs.8b13192 (free Supporting Information)



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Abstract

CHAMPO, a new aminoxyl radical catalyst, enables an electrochemical diazidation of a broad range of alkenes in good yields. Mediated by an anodically generated charge-transfer complex in the form of CHAMPO-N3, radical diazidation was achieved without the need for a transition metal catalyst or a chemical oxidant.

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proposed reaction pathway



Key Words

diazidation, electrochemistry, organocatalysis


ID: J48-Y2019