Electrochemical Synthesis of Imidazo‐Fused N‐Heteroaromatic Compounds through a C−N Bond‐Forming Radical Cascade

Hou, Zhufeng; Mao, Zhong‐Yi; Melcamu, Yared Yohannes; Lü, Xin; Xu, Hai‐Chao

doi:10.1002/ange.201711876

Cited by 45 publications

(9 citation statements)

References 54 publications

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“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14] Compared with other catalytic methods, electrolysis possesses many advantages, including energy economy, cost-efficiency, sustainability, high reactivity and chemoselectivity, mild reaction conditions, broad substrate scope, and scalability, making it a practical technique. [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33] Despite these benefits, most electrochemical transformations only exploit one of the two half-reactions to afford the desired products, while the other side usually undergoes a redox process of solvent, electrolyte, or sacrificial electrodes (Scheme 1a and 1b). 6 In contrast, paired electrolysis is a more attractive method in which the half-reactions at both anode and cathode contribute simultaneously to the formation of the desired products, thus improving the atom economy and energy efficiency of the catalytic process.…”

Section: Introductionmentioning

confidence: 99%

Merging Electrolysis and Nickel Catalysis in Redox Neutral Cross-Coupling Reactions: Experiment and Computation for Electrochemically Induced C–P and C–Se Bonds Formation

et al. 2020

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We have achieved a nickel-catalyzed cross-coupling reaction via concerted paired electrolysis under mild reaction conditions. In this electrochemical transformation, the anodic oxidation of Ni II to Ni III and cathodic reduction of Ni I to Ni 0 occurred simultaneously, resulting in an economical and sustainable cross-coupling protocol. Moreover, we performed mechanistic investigations, achieved by experiments and density functional theory (DFT) calculations for different C-heteroatom bond formations to reveal the catalytic cycle in more detail.

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Section: Introductionmentioning

confidence: 99%

Merging Electrolysis and Nickel Catalysis in Redox Neutral Cross-Coupling Reactions: Experiment and Computation for Electrochemically Induced C–P and C–Se Bonds Formation

et al. 2020

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“…When 40 was electrolyzed at a constant current in a mixed solvent of methyl cyanide and water under reflux in the vicinity of N 2 Ar 4 -catalyst, the best results were achieved. Despite their widespread availability, tetraarylhydrazines have never been used as a redox catalyst. , The required imidazopyridine 41 was extracted in 89% yield under these circumstances …”

Section: Electrosynthesis Of S- N- O-heterocyclesmentioning

confidence: 99%

Heterocyclic Electrochemistry: Renewable Electricity in the Construction of Heterocycles

et al. 2023

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Numerous applications in the realm of biological exploration and drug synthesis can be found in heterocyclic chemistry, which is a vast subject. Many efforts have been developed to further improve the reaction conditions to access this interesting family to prevent employing hazardous ingredients. In this instance, it has been stated that green and environmentally friendly manufacturing methodologies have been introduced to create N-, S-, and O-heterocycles. It appears to be one of the most promising methods to access these types of compounds avoiding use of stoichiometric amounts of oxidizing/reducing species or precious metal catalysts, in which only catalytic amounts are sufficient, and it represent an ideal way of contributing toward the resource economy. Thus, renewable electricity provides clean electrons (oxidant/reductant) that initiate a reaction cascade via producing reactive intermediates that facilitate in building new bonds for valuable chemical transformations. Moreover, electrochemical activation using metals as catalytic mediators has been identified as a more efficient strategy toward selective functionalization. Thus, indirect electrolysis makes the potential range more practical, and less side reactions can occur. The latest developments in using an electrolytic strategy to create N-, S-, and O-heterocycles are the main topic of this mini review, which was documented over the last five years.

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“…Thus, abiding by the principles of green chemistry [108a,b] . There are different reactions that have been carried out under electrochemical conditions such as alkyne functionalization, [109a,b] alkene functionalization, [109c] cascade cyclization, [109d–f] C−H activation, [110a] and halogenation [110b] . Electrochemical conditions could aid redox reactions using electrical energy as a reagent without the presence of transition‐metal catalysts or toxic reagents.…”

Section: Overview On Selenium‐catalyzed/selenium Incorporating Transfmentioning

confidence: 99%

Insights into the Recent Synthetic Advances of Organoselenium Compounds

2021

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The ever-growing interest for organoselenium compounds amongst the chemists has made commendable impact in the field of medicinal chemistry, material chemistry, chemical biology and biochemistry. Researchers have progressively contributed in the development of organoselenium compounds over the years which has been periodically reviewed. On the similar note, this review attempts at providing an overview of the recent advances made in organoselenium chemistry while covering their catalytic indulgence in different transformational approaches, their role in asymmetric synthesis, and synthetic approaches steering their synthesis. These approaches encompass selenofunctionalization and/or cyclization, electrochemical selenylation, bromolactonization, [2,3]-or [1,2]-sigmatropic rearrangement reactions among others. Herein, we have focused on the synthetic approaches developed for the past three years that have not been covered in previously reviewed scientific material. With the knowledge of the recent progress covered, this review could contribute towards future development of organoselenium compounds along with the improvement of the current status.

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Electrochemical Synthesis of Imidazo‐Fused N‐Heteroaromatic Compounds through a C−N Bond‐Forming Radical Cascade

Cited by 45 publications

References 54 publications

Merging Electrolysis and Nickel Catalysis in Redox Neutral Cross-Coupling Reactions: Experiment and Computation for Electrochemically Induced C–P and C–Se Bonds Formation

Merging Electrolysis and Nickel Catalysis in Redox Neutral Cross-Coupling Reactions: Experiment and Computation for Electrochemically Induced C–P and C–Se Bonds Formation

Heterocyclic Electrochemistry: Renewable Electricity in the Construction of Heterocycles

Insights into the Recent Synthetic Advances of Organoselenium Compounds

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