2020
DOI: 10.1021/jacs.9b13918
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Electrocatalytic C–N Coupling via Anodically Generated Hypervalent Iodine Intermediates

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 intraand intermolecular C-N bond-forming reactions. Available mechanistic data indicates that anodic oxidation of aryl iodides generates a transient I(… Show more

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Cited by 77 publications
(82 citation statements)
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“…This approach, pioneered by Ochiai & Miyamoto [5] and by Kita [6] in 2005, de facto establishes iodoarenes as a particular subclass of organocatalysts, [7][8][9] with many synthetic applications, including asymmetric versions. [10,11] Apart from anodic oxidation, which, more than 20 years after the pioneering studies by Fujita, [12] currently receives increasing attention, [13][14][15][16][17][18][19] iodoarene catalysis requires the use of a stoichiometric oxidant, [8] thus generating an equimolar quantity of inorganic or organic waste (Scheme 1 b). A more desirable alternative is the use of molecular oxygen as a widely available and cheap stoichiometric oxidant that would only generate aqueous waste (Scheme 1 c).…”
mentioning
confidence: 99%
“…This approach, pioneered by Ochiai & Miyamoto [5] and by Kita [6] in 2005, de facto establishes iodoarenes as a particular subclass of organocatalysts, [7][8][9] with many synthetic applications, including asymmetric versions. [10,11] Apart from anodic oxidation, which, more than 20 years after the pioneering studies by Fujita, [12] currently receives increasing attention, [13][14][15][16][17][18][19] iodoarene catalysis requires the use of a stoichiometric oxidant, [8] thus generating an equimolar quantity of inorganic or organic waste (Scheme 1 b). A more desirable alternative is the use of molecular oxygen as a widely available and cheap stoichiometric oxidant that would only generate aqueous waste (Scheme 1 c).…”
mentioning
confidence: 99%
“…Apart from anodic oxidation, which, more than 20 years after the pioneering studies by Fujita, [12] currently receives increasing attention, [13–19] iodoarene catalysis requires the use of a stoichiometric oxidant, [8] thus generating an equimolar quantity of inorganic or organic waste (Scheme 1 b). A more desirable alternative is the use of molecular oxygen as a widely available and cheap stoichiometric oxidant that would only generate aqueous waste (Scheme 1 c).…”
Section: Methodsmentioning
confidence: 99%
“…This process has been coupled with oxidative C–H/N–H coupling for the development of an electrocatalytic amination of arenes (Fig. 1c ) 13 . Obviously, the electrocatalytic generation of I(III) species holds great potential for many other oxidation processes.…”
Section: Electrocatalytic Transformations Based On Hypervalent Iodinementioning
confidence: 99%