Chem Catalysis, Год журнала: 2023, Номер 3(5), С. 100619 - 100619
Опубликована: Май 1, 2023
Язык: Английский
Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(16), С. 1921 - 1930
Опубликована: Апрель 7, 2023
Comprehensive Summary The radical‐mediated reductive functionalization of aryl halides has been extensively studied. However, the related intermolecular 1,2‐diarylation alkenes, using as radical sources, remains unexplored. Herein, a new electrophotocatalytic alkenes is reported and cyanoaromatics to produce polyarylated alkanes. Using synergistic cathodic reduction visible‐light photoredox catalysis, various electron‐rich electron‐deficient are combined with characterize broad substrate scope, excellent functional group compatibility, selectivity this reaction. Mechanistic investigations reveal that reaction may proceed via process initiated by generation radicals from terminated radical‐radical coupling cyanoaromatic anions.
Язык: Английский
Процитировано
36
Nature Communications, Год журнала: 2023, Номер 14(1)
Опубликована: Март 17, 2023
With the fast development of synthetic chemistry, introduction functional group into organic molecules has attracted increasing attention. In these reactions, difunctionalization unsaturated bonds, traditionally with one nucleophile and electrophile, is a powerful strategy for chemical synthesis. this work, we develop different path electrochemical oxidative diazo compounds two nucleophiles. Under metal-free external oxidant-free conditions, series structurally diverse heteroatom-containing hardly synthesized by traditional methods (such as high-value alkoxy-substituted phenylthioacetates, α-thio, α-amino acid derivatives well α-amino, β-amino derivatives) are obtained in synthetically useful yields. addition, procedure exhibits mild reaction excellent functional-group tolerance good efficiency on large-scale Importantly, protocol also amenable to key intermediate bioactive simple practical process.
Язык: Английский
Процитировано
31
The Chemical Record, Год журнала: 2025, Номер unknown
Опубликована: Фев. 3, 2025
Abstract Owing to their wide utilizations in synthesis and products prevalence numerous natural products, pharmaceuticals functional materials, the alkene difunctionalization methods for selective transformations of olefins are important have attracted much attention form synthetic chemists. Among them, electrochemical reaction is particularly promising has becoming a potent sustainable tool alkenes into vicinal difunctionalized structures organic through simultaneous incorporation two groups. Herein, we summarize recent progress reactions according types as well category radicals over past five years. By selecting remarkable examples, elaborately discussed substrate scope mechanisms olefin reaction.
Язык: Английский
Процитировано
1
The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(19), С. 13790 - 13799
Опубликована: Сен. 22, 2021
The oxidation of diaryl sulfides and aryl alkyl to the corresponding sulfoxides sulfones under electrochemical conditions is reported. Sulfoxides are selectively obtained in good yield a constant current 5 mA for 10 h DMF, while formed as major product or 20 MeOH. oxygen both sulfoxide sulfone function derived from water.
Язык: Английский
Процитировано
46
ACS Catalysis, Год журнала: 2022, Номер 12(6), С. 3309 - 3316
Опубликована: Фев. 25, 2022
The reduction of epoxides is a powerful tool to access anti-Markovnikov alcohols, but reported methods are poorly compatible with strongly electronically deactivated substrates. Here, we describe general method for the linear-selective styryl oxides incorporating strong electron-withdrawing groups. remains more traditional epoxide motifs, such as aliphatic and electron-rich styrene oxides. Other (hetero)cycles oxetanes, tetrahydrofurans, aziridines, cyclopropanes can also be reductively opened. This user-friendly reaction relies on combination Brønsted acid catalyst hexafluoroisopropanol solvent, thus, in contrast existing methods, it does not require anhydrous reagents or an inert atmosphere. generated primary alcohols conveniently functionalized situ by dehydrative Friedel–Crafts arylation without preactivation.
Язык: Английский
Процитировано
30
Synthesis, Год журнала: 2023, Номер 55(18), С. 2843 - 2859
Опубликована: Фев. 15, 2023
Abstract The electrochemical alkene difunctionalization reaction has become a powerful and sustainable tool for the efficient construction of vicinal difunctionalized structures in organic synthesis. Since only electrons are used as redox agents, avoids need additional catalysts, metal or chemical oxidants does not generate waste. Herein we summarize latest contributions alkenes over last 3–4 years. We discuss detail features, scope, limitations, mechanistic rationalizations three categories methods: (1) terminated by nucleophiles, (2) radicals, (3) functionality migration. 1 Introduction 2 Electrochemical Alkene Difunctionalization Terminated Nucleophiles 2.1 Sulfonylative Alkenes 2.2 Sulfurizative/Sulfoxidative 2.3 Azidotetrazolation 2.4 Trifluoromethylative 2.5 Diarylation 3 Radicals 3.1 Direct Radical-Coupling-Enabled 3.2 Metal-Mediated Radical Transfer Coupling Enabled 3.3 Metalloid-Mediated 4 Functionality Migration 5 Summary Outlook
Язык: Английский
Процитировано
23
Advanced Materials, Год журнала: 2023, Номер 35(49)
Опубликована: Март 25, 2023
Polycyclic aromatic hydrocarbons (PAHs) have surfaced as increasingly viable components in optoelectronics and material sciences. The development of highly efficient atom-economic tools to prepare PAHs under exceedingly mild conditions constitutes a long-term goal. Traditional syntheses largely relied on multistep approaches or the conventional Scholl reaction. However, reactions are inefficient with electron-deficient substrates, require stoichiometric chemical oxidants, typically occur presence strong acid. In sharp contrast, electrochemistry has gained considerable momentum during past decade an alternative for facile straightforward assembly, generally via electro-oxidative dehydrogenative annulation, releasing molecular hydrogen sole byproduct by evolution This review provides overview recent significant advances field electrochemical various until January 2023.
Язык: Английский
Процитировано
18
Chemistry - A European Journal, Год журнала: 2023, Номер 29(36)
Опубликована: Апрель 18, 2023
Herein, a nickela-electrocatalyzed cross-electrophile coupling of readily available aryl aziridines and bromides under mild sustainable electrochemical conditions to access synthetic useful β-arylethylamines is developed. This protocol characterized by its exquisite chemo- regioselectivity, broad substrate scope good functional group compatibility. Mechanistic studies confirmed that the regioselectivity reactivity observed are result electro-induced ring-opening electroreductive generate benzyl radical intermediate as active species. Furthermore, this strategy also enables cross-coupling with CO2 β-amino acids conditions.
Язык: Английский
Процитировано
18
Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4318 - 4342
Опубликована: Янв. 1, 2024
This review primarily focuses on the generation of aryl radicals via an electroreduction strategy, and systematically elaborates synthetic applications, scope, limitations substrates.
Язык: Английский
Процитировано
9
Nature Communications, Год журнала: 2024, Номер 15(1)
Опубликована: Ноя. 8, 2024
Aryl thianthrenium salts are valuable in photocatalysis but traditionally require external electron donors for activation. This study introduces an energy transfer (EnT) strategy the activation of aryl using 2,3,4,5,6-penta(carbazol-9-yl)benzonitrile (5CzBN) as a metal-free photocatalyst, eliminating need donors. Utilizing this EnT approach, we achieve C-H deuteration arenes under visible light with CDCl
Язык: Английский
Процитировано
9