Benzylic C–H arylation with dicyanoarenes<i>via</i>convergent paired electrolysis

Tang, Shanyu; Vincent, Guillaume

doi:10.1039/d3gc00866e

Cited by 5 publications

(1 citation statement)

References 58 publications

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“…Organic electrochemistry relies on electrons to drive redox processes, which is more sustainable and tunable than the use of chemical oxidants and reductants . In this context, a range of efficient benzylic C(sp 3 )–H bond functionalizations have been established under mild electrochemical conditions, such as amination (Scheme a), oxidation, azidation, cyanation, arylation, and acyloxylation . Recently, Powers and co-workers reported a benzylic C–H N -aminopyridylation under thermolysis or photolysis conditions in the presence of superstoichiometric oxidant DDQ or NIS (Scheme b) .…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Benzylic C–H Amination via N-Aminopyridinium

Liu,

Du,

Zhang

et al. 2024

J. Org. Chem.

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An electrochemical protocol for benzylic C(sp 3 )−H aminopyridylation via direct C−H/N−H cross-coupling of alkylarenes with N-aminopyridinium triflate has been developed. This method features excellent site-selectivity, broad substrate scope, redox reagent-free and facile scalability. The generated benzylaminopyridiniums can be readily converted to benzylamines via electroreductive N−N bond cleavage.

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Section: Introductionmentioning

confidence: 99%

Electrochemical Benzylic C–H Amination via N-Aminopyridinium

Liu,

Du,

Zhang

et al. 2024

J. Org. Chem.

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Site‐Selective Pyridination of Benzylic and Allylic C−H bonds via Radical‐Radical Cross‐Coupling

Chen,

Wang,

Huang

2024

Adv Synth Catal

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The development of site‐selective radical reaction is a long‐standing challenge in synthetic chemistry. One important advance in this area has been the Minisci‐type reaction, which has proven to be a powerful tool for functionalizing medicinally‐relevant heterocycles by allowing nucleophilic carbon radicals to add to heteroarenes. Herein, we report a modular photocatalytic platform for the site‐selective pyridination of saturated hydrocarbon compounds employing organic photoredox catalysis to forge new carbon‐carbon bonds. The site‐selective C―H pyridination could successfully couple benzylic/allylic C―H bonds with pyridylphosphonium salts, which installed directly and regioselectively from C―H heteroarenes through a radical‐radical cross coupling mechanism. This synthetic methodology could tolerance a variety of functional groups, complex heteroarenes, even late‐stage functionalization of pharmaceuticals selectively and efficiently.

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