Tetrahedron Letters, Год журнала: 2023, Номер 121, С. 154460 - 154460
Опубликована: Март 30, 2023
Язык: Английский
Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(22), С. 2963 - 2968
Опубликована: Июнь 24, 2023
Comprehensive Summary A photoelectrochemical approach for the C—H silylation of heteroarenes through dehydrogenation cross‐coupling with H 2 evolution has been developed. The depends on hydrogen atom transfer (HAT) from silanes to Cl‐radical generated light‐induced homolytic cleavage Cl , in which was produced by electrochemical oxidation chloride. large number silylated heterocyclic molecules are rapidly constructed satisfactory yields without relying oxidants and metal reagents.
Язык: Английский
Процитировано
39
The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(3), С. 1625 - 1634
Опубликована: Янв. 25, 2023
In this article, an electrochemical method for the direct synthesis of β-amino alcohols from imines and ketones is described. Mechanistic studies, including a radical trapping experiment, electron paramagnetic resonance, cyclic voltammetry, divided-cell electrolysis support radical-involved reductive cross coupling with at cathode. The use abundant easily prepared starting materials, high atom- step-economy, insensitivity to air moisture make synthetic strategy more efficient construction various alcohol derivatives.
Язык: Английский
Процитировано
11
Green Chemistry, Год журнала: 2023, Номер 25(13), С. 5128 - 5133
Опубликована: Янв. 1, 2023
A unique electrochemical four-component reaction of terminal alkynes, (thio)xanthenes, nitriles, and water has been established in the absence any catalyst or external oxidant.
Язык: Английский
Процитировано
11
Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown
Опубликована: Авг. 21, 2024
We disclose a benzylic C-H oxidative coupling reaction with alcohols that proceeds through synergistic deprotonation, halogenation and substitution sequence. The combination of tert-butoxide bases 2-halothiophene halogen oxidants enables the first general protocol for generating using benzyl halides deprotonative pathway. In contrast to existing radical-based methods functionalization, this process is guided by acidity trends. This gives rise new synthetic capabilities, including ability functionalize diverse methyl(hetero)arenes, tolerance oxidizable nucleophilic functional groups, precision site-selectivity polyalkylarenes use double etherification controllably oxidize methylarenes benzaldehydes.
Язык: Английский
Процитировано
4
Advanced Science, Год журнала: 2025, Номер unknown
Опубликована: Апрель 26, 2025
Abstract Electrooxidative coupling of C(sp 3 )─H bonds with nucleophiles offers an attractive method for constructing C─C and C─X without sacrificial oxidants. However, the direct electrochemical approach requires nucleophilic reagent to have a higher potential than partners, which restricts substrate scope. In this study, quinoline derivative is introduced as mediator, enabling efficient C─H bond etherification reduced reliance on electronic properties substrates. The catalytic system demonstrates broad compatibility, extending partners featuring diverse range bonds, including tertiary benzylic unactivated bonds. Mechanistic investigations confirm role electrocatalyst in hydrogen atom transfer (HAT) process. This provides versatile strategy late‐stage functionalization bioactive molecules.
Язык: Английский
Процитировано
0
The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(5), С. 2985 - 2998
Опубликована: Фев. 22, 2023
This report describes a mild electrochemical α-oxygenation of wide range linear and cyclic benzamides mediated by N-hydroxyphthalimide (NHPI) in an undivided cell using O2 as the oxygen source 2,4,6-trimethylpyridine perchlorate electrolyte. The radical scavenger experiment 18O labeling were carried out, which indicated involvement pathway suggested imides, respectively.
Язык: Английский
Процитировано
10
Chemistry - A European Journal, Год журнала: 2024, Номер 30(20)
Опубликована: Фев. 7, 2024
Abstract The electrochemical oxidative dearomatizing methoxylation of phenols and naphthols was developed. It provides an alternative route for the preparation methoxycyclohexadienones, important versatile synthetic intermediates, that eliminates need stoichiometric high‐energy chemical oxidants generates hydrogen as a sole by‐product. reaction proceeds in simple constant current mode, undivided cell, it employs standardized instrumentation. A collection methoxycyclohexadienones derived from various 2,4,6‐tri‐substituted 1‐substituted‐2‐naphthols obtained moderate to excellent yields. These include complex derivative estrone, well methoxylated dearomatized 1,1′‐bi‐2‐naphthols (BINOLs). mechanism subject profound investigations using density functional theory calculations. In particular, reactivity two key phenoxyl radical phenoxenium ion, carefully examined. results shed light on pathway leading desired product rationalize experimentally observed selectivities regarding side benzylic preference functionalization at para over ortho position. They also uncover structure‐selectivity relationship, inversely correlating steric bulk substrate with its propensity undergo side‐reaction. Moreover, loss stereochemical information enantiopure BINOL substrates during is rationalized by computations.
Язык: Английский
Процитировано
3
Green Chemistry, Год журнала: 2022, Номер 24(20), С. 7883 - 7888
Опубликована: Янв. 1, 2022
An electrochemical benzylic C(sp 3 )–H cross-coupling with organotrifluoroborates without any catalyst or external electrolyte has been developed.
Язык: Английский
Процитировано
14
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(6), С. 4145 - 4155
Опубликована: Фев. 28, 2024
The environmental benefits of molecular oxygen as the oxidizing agent in oxidation reactions that synthesize fine chemicals cannot be overstated. Increased interest developing robust photocatalysts is stimulated by fact current photocatalytic transformation boom has made previously inaccessible synthetic approaches possible. Motivated enzymatic catalysis, employing a reusable phenalenyl-based photocatalyst, we have successfully developed oxidative dehydrogenation utilizing greener oxidant. Under photoinduced conditions, different types saturated N-heterocycles and alcohols were dehydrogenated. versatility this bioinspired protocol demonstrated wide variety N-heteroaromatics, such quinoline, carbazole, quinoxaline, acridine, indole derivatives, well aldehydes ketones, synthesized. Detailed mechanistic studies validate proposed mechanism. Fluorescence lifetime CV experiments revealed crucial role water on efficiency reaction. present also provides chemoselectivity scalability, leading to superior results allowing for functionalization bioactive molecules at late stage sustainable manner.
Язык: Английский
Процитировано
2
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(44)
Опубликована: Июль 30, 2024
Abstract This Minireview examines a selection of case studies that showcase distinctive and enabling electrochemical approaches have allowed for the generation reaction carbocation intermediates under mild conditions. Particular emphasis is placed on progress has been made in this area organic synthesis polymer chemistry over past decade.
Язык: Английский
Процитировано
2