Electrocatalytic C-N Coupling via Anodically Generated Hypervalent Iodine Intermediates

Journal of the American Chemical Society
Asim MaityDavid C Powers

Abstract

Development of new electrosynthetic chemistry promises to impact the efficiency and sustainability of organic synthesis. Here we demonstrate that anodically generated hypervalent iodine intermediates effectively couple interfacial electron transfer with oxidative C-H/N-H coupling chemistry. The developed hypervalent iodine electrocatalysis is applicable in both intra- and intermolecular C-N bond-forming reactions. Available mechanistic data indicate that anodic oxidation of aryl iodides generates a transient I(II) intermediate that is critically stabilized by added acetate ions. This report represents the first example of metal-free hypervalent iodine electrocatalysis for C-H functionalization and provides mechanistic insight that we anticipate will contribute to the development of hypervalent iodine mediators for synthetic electrochemistry.

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Citations

Jul 31, 2020·Nature Communications·José M Lassaletta
Dec 2, 2020·Chemistry : a European Journal·Yuya NakatsujiYoshiji Takemoto
Aug 2, 2020·Chemistry : a European Journal·Anton KehlSiegfried R Waldvogel
May 2, 2021·Chemistry : a European Journal·Mahesh PuthanveeduAndrey P Antonchick
May 7, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Sara Cembellín, Belén Batanero
Apr 25, 2021·Angewandte Chemie·Igors SokolovsEdgars Suna
Oct 8, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yan GaoYan-Na Ma
Nov 13, 2021·The Journal of Organic Chemistry·Sayad DoobaryAlastair J J Lennox

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