Hydropyridylation of α,β-Unsaturated Esters through Electroreduction of 4-Cyanopyridine

Zhou, Hongyu; Huang, Jing‐Mei

doi:10.1021/acs.joc.2c00177

Cited by 8 publications

(3 citation statements)

References 48 publications

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“…On the basis of the aforementioned experimental results and the related literature reports, a plausible mechanism was proposed in Scheme . First, the protonation of 1,4-dicyanobenzene ( 2a ) with HFIP yielded the benzylidyne ammonium intermediate ( IM1 ), followed by a cathodic reduction to produce the carbon-centered radical intermediate ( IM2 ), which attacked the C3 position of 1-methylquinoxalin-2(1 H )-one ( 1a ) to generate the nitrogen-centered radical intermediate ( IM3 ).…”

Section: Resultsmentioning

confidence: 97%

Paired Electrolysis-Enabled Arylation of Quinoxalin-2(1H)-ones

Hou,

Jiang,

Wen

et al. 2024

J. Org. Chem.

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The first paired electrolysis-enabled arylation of quinoxalin-2(1H)-ones was achieved using cyanoarenes as the arylation reagents. A variety of 3-arylquinoxalin-2(1H)-ones with various important functional groups were obtained in moderate to good yields under metal-and chemical oxidant-free conditions. With a pair of reductive and oxidative processes occurring among the substrates and reaction intermediates, the power consumption can be dramatically reduced.

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Section: Resultsmentioning

confidence: 97%

Paired Electrolysis-Enabled Arylation of Quinoxalin-2(1H)-ones

Hou,

Jiang,

Wen

et al. 2024

J. Org. Chem.

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“…Additionally, Huang et al. described an easy and effective electrochemical method for producing pyridine derivatives from enones, aldehydes, and α,β‐unsaturated esters (Scheme 45d) [148] …”

Section: Electro‐catalyzed Radical Decyanative Transformationsmentioning

confidence: 99%

Radical Decyanations of Unactivated Carbon‐CN Bonds: Recent Achievements and Mechanistic Studies

Huang

Chen

2023

Adv Synth Catal

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Decyanation is an important process in the synthesis of aromatic molecules in the studies of pharmaceutical research, medical and materials sciences. In late‐stage modifications of privileged carbo/heterocyclic scaffolds, radical‐type decyanation techniques have been devised to date. As a result, the chemistry of cyano‐involved conversions, a hotly debated subject over the past few decades, has advanced significantly. The cyano group (CN), on the other hand, has rarely been acknowledged as a good reaction site due to its thermodynamic robustness. The most recent advancements in catalytic radical decyanation protocols that CN behaved as a leaving group has made are surveyed in this article. Following the introduction of a number of different reaction modes, the catalytic reactions that are used to activate the C−CN bonds are primarily categorized, and the text herein are divided into three groups: (1) photo‐catalyzed decyanation transformations, (2) electro‐catalyzed decyanation transformations, and (3) transition‐metal‐catalyzed or metal‐free decyanation transformations. With an emphasis on the catalytic systems and synthetic applications in C−CN bond activation, this review will provide the readers with an overview of decyanation chemistry in radical reactions.

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“…Next, we performed the cyclic voltammetry experiments to understand more mechanistic details. As shown in Figure -2, the CV of quinoline A1 gave a clear indication of a reversible redox process, and two reduction peaks were observed [Figure -2a; −2.38 and −2.78 V in DMF vs a saturated calomel electrode (SCE)], whereas the acetophenone B1 showed one reduction potential of −2.15 V. Then, the addition of sufficient ZnI 2 into quinoline A1 or acetophenone B1 in DMF resulted in the same reduction potential of −1.75 V (Figure -2b–d), the positive shift of the reduction potentials was assigned to the coordination of zinc cation with A1 and B1 , , and the zinc ion activated both reactants to make their reduction easier. Such a coordination was further proved by NMR analyses (Figure S9), as the presence of ZnI 2 resulted in an obvious proton chemical shift for reactants A1 and B1 .…”

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confidence: 99%

Room Temperature Construction of Vicinal Amino Alcohols via Electroreductive Cross-Coupling of N-Heteroarenes and Carbonyls

Wang

Zhang

et al. 2023

J. Am. Chem. Soc.

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Despite the widespread applications of α-hydroxyalkyl cyclic amines, direct and diverse access to such a class of unique vicinal amino alcohols still remains, to date, a challenge. Here, through a strategy of electroreductive α-hydroxyalkylation of inactive N-heteroarenes with ketones or electron-rich arylaldehydes, we describe a room temperature approach for the direct construction of α-hydroxyalkyl cyclic amines, which features a broad substrate scope, operational simplicity, high chemoselectivity, and no need for pressurized H 2 gas and transition metal catalysts. The zinc ion generated from anode oxidation plays a crucial role in the activation of both reactants by decreasing their reduction potentials. The strategy of electroreduction in combination with substrate activation by Lewis acids in this work is anticipated to develop more useful transformations.

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Hydropyridylation of α,β-Unsaturated Esters through Electroreduction of 4-Cyanopyridine

Cited by 8 publications

References 48 publications

Paired Electrolysis-Enabled Arylation of Quinoxalin-2(1H)-ones

Paired Electrolysis-Enabled Arylation of Quinoxalin-2(1H)-ones

Radical Decyanations of Unactivated Carbon‐CN Bonds: Recent Achievements and Mechanistic Studies

Room Temperature Construction of Vicinal Amino Alcohols via Electroreductive Cross-Coupling of N-Heteroarenes and Carbonyls

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