Palladium‐Catalyzed C−H Iodination of N‐(8‐Quinolinyl)benzamide Derivatives Under Electrochemical and Non‐Electrochemical Conditions

Abstract

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Electrochemical strategies for C–H functionalization and C–N bond formation

“…It was proposed that anodic oxidation of the halide ion produces a halonium ion, which subsequently reacts with the generated palladacycle to provide the halogenated product while regenerating the Pd II catalyst. [517][518][519][520] Expanding on this concept, the Kakiuchi group disclosed a method for regioselective homocoupling of arylpyridines in the presence of I 2 employing electrooxidative Pd catalysis. 521 Additionally, protocols for perfluoroacetoxylation, 522 perfluoroalkylation 523,524 and phosphorylation 525,526 of arylpyridines have been established by the Budnikova group.…”

Decoding Directing Groups and Their Pivotal Role in C−H Activation

“…[180] Kakiuchi group has been focused in palladium-catalyzed electrochemical oxidative CÀ H halogenation of benzamides. [181,182] The employment of electric current as redox equivalent avoiding stoichiometric amounts of toxic and costly chemical redox reagents, has been well utilized by Kakiuchi in his work. [183] They described an example of ortho-iodination of N-quinolyl benzamides using I 2 .…”

“…Other method demonstrated from Daugulis and co‐workers showed a copper‐catalyzed ortho ‐amination of benzamides with morpholine in moderate yields [180] . Kakiuchi group has been focused in palladium‐catalyzed electrochemical oxidative C−H halogenation of benzamides [181,182] . The employment of electric current as redox equivalent avoiding stoichiometric amounts of toxic and costly chemical redox reagents, has been well utilized by Kakiuchi in his work [183] .…”

Palladium‐Catalyzed Aromatic C−H Functionalizations Utilizing Electrochemical Oxidations

“…The palladium‐catalyzed electrochemical C−H iodination was also examined for N ‐(5,7‐dichloroquinolin‐8‐yl)benzamides, [16] which was applicable to the C−H chlorination as described in section 2.2 [13] . The C−H iodination of benzamide 8 j conducted using DMF as a solvent provided the corresponding ortho iodination product 17 j in 91 % yield (entry 1, Table 3).…”