Electrochemical ammonium-cation-assisted pyridylation of inert N-heterocycles via dual-proton-coupled electron transfer

Niu, Cong; Yang, Jianjing; Yan, Kelu; Xie, Jiafang; Jiang, Wei; Li, Bingwen; Wen, Jiangwei

doi:10.1016/j.isci.2022.104253

Cited by 7 publications

(10 citation statements)

References 51 publications

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“…However, these electron-deficient pyridine derivatives compounds are difficult to activate due to their inherently negative electrode potential. Our exploring the dual proton-coupled electron transfer (PCET) strategy may provide a promising roadmap for the electrochemical pyridylation of inert N-heterocycles with cyanopyridines ( Niu et al., 2022 ).…”

Section: Before You Beginmentioning

confidence: 99%

“…Herein, the current protocol describes the first straightforward and practical strategy for the pyridylation of electron-deficient quinolines aided by NH 4 + in an undivided cell via the dual PCET followed by the radical cross-coupling in mmol scale. For the same experiment performed in batch, please refer to Niu et al. (2022) .…”

Section: Before You Beginmentioning

confidence: 99%

“…L.B. performed theoretical calculations in Niu et al (2022) . All the authors discussed the results of the manuscript.…”

Section: Acknowledgmentsmentioning

confidence: 99%

“…The protocol is limited to cyanopyridines. For complete details on the use and execution of this protocol, please refer to Niu et al. (2022) .…”

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confidence: 99%

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An electrochemical gram-scale protocol for pyridylation of inert N-heterocycles with cyanopyridines

et al. 2022

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Section: Before You Beginmentioning

confidence: 99%

Section: Before You Beginmentioning

confidence: 99%

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An electrochemical gram-scale protocol for pyridylation of inert N-heterocycles with cyanopyridines

et al. 2022

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“…Secondly, suitable use of the mechanism of proton-coupled electron transfer (PCET) in proton rich electrochemical systems can pull the potentials of the substrates closer to resolving the potential mismatch. 3 i ,6…”

Section: Introductionmentioning

confidence: 99%

Precise manipulation of electron transfers to enable the site-selective hydropyridylation of ynones

Yang

Yan

et al. 2023

Org. Chem. Front.

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Cathodically Coupled Electrolysis to Access Biheteroaryls

He,

Liang,

Cheng

et al. 2024

Org. Lett.

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An electrochemical approach to biheteroaryls through the coupling of diverse N-heteroarenes with heteroaryl phosphonium salts is reported. The reaction features pH and redox-neutral conditions and excellent regioselectivity, as well as exogenous air or moisture tolerance. Additionally, a one-pot, two-step protocol can be established to realize formal C−H/C−H coupling of heteroarenes, thereby greatly expanding the substrate availability. The utility of this method is demonstrated through late-stage functionalization, the total synthesis of nitraridine, and antifungal activity studies.B iheteroaryls constitute cardinal motifs in various natural products, ligands, agrochemicals, and pharmaceuticals (Scheme 1A). 1 Therefore, the construction of these scaffolds has received extensive attention (Scheme 1B). Classically, biheteroaryls are prepared via transition-metal-catalyzed crosscoupling approaches. 2 A number of alternative protocols toward challenging biheteroaryls have consequently been developed by capitalizing on C−H arylation processes, 3 cross-dehydrogenative couplings, 4 sulfur(IV)-mediated cross-

show abstract

Electrochemical ammonium-cation-assisted pyridylation of inert N-heterocycles via dual-proton-coupled electron transfer

Cited by 7 publications

References 51 publications

An electrochemical gram-scale protocol for pyridylation of inert N-heterocycles with cyanopyridines

An electrochemical gram-scale protocol for pyridylation of inert N-heterocycles with cyanopyridines

Precise manipulation of electron transfers to enable the site-selective hydropyridylation of ynones

Cathodically Coupled Electrolysis to Access Biheteroaryls

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