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• W4285999712 endingPage "13919" @default.
• W4285999712 startingPage "13913" @default.
• W4285999712 abstract "Small molecule redox mediators convey interfacial electron transfer events into bulk solution and can enable diverse substrate activation mechanisms in synthetic electrocatalysis. Here, we report that 1,2-diiodo-4,5-dimethoxybenzene is an efficient electrocatalyst for C-H/E-H coupling that operates at as low as 0.5 mol % catalyst loading. Spectroscopic, crystallographic, and computational results indicate a critical role for a three-electron I-I bonding interaction in stabilizing an iodanyl radical intermediate (i.e., formally I(II) species). As a result, the optimized catalyst operates at more than 100 mV lower potential than the related monoiodide catalyst 4-iodoanisole, which results in improved product yield, higher Faradaic efficiency, and expanded substrate scope. The isolated iodanyl radical is chemically competent in C-N bond formation. These results represent the first examples of substrate functionalization at a well-defined I(II) derivative and bona fide iodanyl radical catalysis and demonstrate one-electron pathways as a mechanistic alternative to canonical two-electron hypervalent iodine mechanisms. The observation establishes I-I redox cooperation as a new design concept for the development of metal-free redox mediators." @default.
• W4285999712 created "2022-07-21" @default.
• W4285999712 creator A5056784841 @default.
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• W4285999712 date "2022-07-20" @default.
• W4285999712 modified "2023-10-01" @default.
• W4285999712 title "Iodine–Iodine Cooperation Enables Metal-Free C–N Bond-Forming Electrocatalysis via Isolable Iodanyl Radicals" @default.
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• W4285999712 doi "https://doi.org/10.1021/jacs.2c05562" @default.
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• W4285999712 hasPublicationYear "2022" @default.
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