Electrochemical Catalytic Hydrocarbonylation of Arylacetylenes DOI

Jiaoyan Zhao,

Hongyan Yuan, Ruonan Chen

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2021, Номер 11(2)

Опубликована: Дек. 15, 2021

Abstract An efficient and environmentally‐friendly synthesis of aryl ketones through the electrochemical catalytic hydrocarbonylation arylacetylene is demonstrated. The reaction conditions are mild without transition metal catalysts, extra oxidants, or strong acids involved. By using Selectfluor as additive, this transformation exhibits good functional‐group tolerance. ketone product obtained with up to 90% isolated yield in mixed electrolytes acetonitrile water. This method may open a new window for green from arylacetylenes.

Язык: Английский

Electrochemical Bromofunctionalization of Alkenes and Alkynes—To Sustainability and Beyond DOI Creative Commons

Lilla G. Gombos,

Siegfried R. Waldvogel

Sustainable Chemistry, Год журнала: 2022, Номер 3(4), С. 430 - 454

Опубликована: Окт. 13, 2022

The electrochemical generation of highly reactive and hazardous bromine under controlled conditions as well the reduction surplus oxidizers reagent waste has placed synthesis in a highlighted position. In particular, dibromination bromofunctionalization alkenes alkynes have received significant attention, forming synthetically important derivatives can be generated from bench-stable safe bromide sources “green” conditions. Readily available non-corrosive salts been utilized with dual role both supporting electrolyte. However, this trend seems to change preparation organobromine species. review, was addressed terms their sustainability.

Язык: Английский

Процитировано

15

Recent Advances in the Electrochemical Functionalization of Isocyanides DOI

Qingyun Gu,

Zhenfeng Cheng,

Xiaodong Qiu

и другие.

The Chemical Record, Год журнала: 2022, Номер 23(1)

Опубликована: Сен. 20, 2022

Abstract Isocyanides are well‐known as efficient CO surrogates and C1 synthons in modern organic synthesis. Although tremendous efforts have been devoted to fully exploiting the reactivity of isocyanides, these transformations primarily limited by their utilization stoichiometric toxic chemical oxidants. With recent resurgence electrochemistry, which has considerably laid dormant over past several decades, electrolysis identified a green powerful tool enrich structural diversity solely utilizing electric current clean inherently safe redox equivalents In this regard, unique isocyanides studied numerous electrochemical transformations. This review comprehensively highlights most relevant progress strategies towards functionalization up until June 2022, with focus on reaction outcomes mechanisms.

Язык: Английский

Процитировано

14

Organocatalytic Electrosynthesis of Cinnolines through Cascade Radical Cyclization and Migration DOI

Chen Cai,

Yi Lu,

Chengcheng Yuan

и другие.

ACS Sustainable Chemistry & Engineering, Год журнала: 2021, Номер 9(50), С. 16989 - 16996

Опубликована: Дек. 7, 2021

A straightforward one-pot two-step electrosynthesis of cinnoline derivatives from ortho-alkynyl acetophenones and sulfonyl hydrazides has been developed through the organocatalytic cascade radical cyclization migration. This methodology features green mild reaction conditions, good to excellent yield, broad functional group tolerance, regioselectivity, use readily available substrates. Moreover, based on isotope labeling, trapping, singlet oxygen superoxide anion inhibiting, cyclic voltammetry, EPR experiments, a possible electrochemically migration process was proposed.

Язык: Английский

Процитировано

19

Electrochemical synthesis of 5-trifluoroethyl dihydrobenzimidazo[2,1-a] isoquinolines from pendent unactivated alkenes via radical relay DOI
Yi Lv,

Jia-Ying Dai,

Zi-Xin Zhao

и другие.

Tetrahedron Letters, Год журнала: 2023, Номер 119, С. 154410 - 154410

Опубликована: Фев. 20, 2023

Язык: Английский

Процитировано

7

Metal-Free C–C Cross Coupling: Electrosynthesis of Azaheterocycles through Anodic Oxidation Cyclization of 1,6-Enynes DOI

Chen Cai,

Yi Lu,

Chengcheng Yuan

и другие.

ACS Sustainable Chemistry & Engineering, Год журнала: 2022, Номер 10(10), С. 3288 - 3294

Опубликована: Март 3, 2022

A straightforward synthesis of azaheterocycles has been developed through electrochemically aerobic oxidation cyclization using a user-friendly undivided electrolytic cell at room temperature under catalyst-free conditions. This green and practical electrosynthesis strategy features good functional group, diverse electronic steric properties tolerance. On the basis series mechanistic investigations, including isotope labeling, singlet oxygen inhibiting, superoxide radical anion radical-trapping, cyclic voltammetry controlled potential electrolysis experiments, possible N-centered radical-initiated mechanism was proposed.

Язык: Английский

Процитировано

12

Electrochemical Generation of Peroxy Radicals and Subsequent Peroxidation of 1,3-Dicarbonyls in an Undivided Cell DOI
Oleg V. Bityukov,

Ksenia V. Skokova,

Vera A. Vil’

и другие.

Organic Letters, Год журнала: 2023, Номер 26(1), С. 166 - 171

Опубликована: Дек. 28, 2023

The generation of peroxy radicals from hydroperoxides with subsequent selective peroxidation 1,3-dicarbonyls in an undivided electrochemical cell under constant current conditions is reported. method provides a variety peroxy-containing barbituric acids and 4-hydroxy-2(5H)-furanones yields up to 74%. Only the combination anodic cathodic processes efficient by generating set alkoxy radicals. NaNO3 acts as both electrolyte redox mediator radical reactions.

Язык: Английский

Процитировано

6

Electrosynthesis of Highly Functionalized Polycyclic N-Heteroaromatics through Cascade Radical Cyclization and Alkoxylation in Batch and Continuous-Flow DOI
Jiawei Chen,

Yaqi Qiao,

Wenjing Guan

и другие.

ACS Sustainable Chemistry & Engineering, Год журнала: 2023, Номер 11(50), С. 17728 - 17738

Опубликована: Дек. 6, 2023

Electrochemical radical cascade cyclization has been recognized as a powerful, straightforward, and environmentally-friendly synthetic tool to give highly functionalized polycyclic aromatic compounds but remains challenging difficult because of the instability intermediates under electrolysis conditions, especially using user-friendly undivided cell. Herein, we report novel electrosynthesis pyridine-fused N-heteroaromatics through dehydrogenative alkoxylation oxidant-free conditions. This electrochemical synthesis methodology features green mild reaction good functional group tolerance, use readily available substrates. Moreover, attributed flow cells, steady production large-scale preparation can be conveniently achieved only small amounts electrolytes.

Язык: Английский

Процитировано

4

Transition-metal-catalyst-free electroreductive alkene hydroarylation with aryl halides under visible-light irradiation DOI Creative Commons
Kosuke Yamamoto,

Kazuhisa Arita,

Masami Kuriyama

и другие.

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 1327 - 1333

Опубликована: Июнь 10, 2024

The radical hydroarylation of alkenes is an efficient strategy for accessing linear alkylarenes with high regioselectivity. Herein, we report the electroreductive electron-deficient and styrene derivatives using (hetero)aryl halides under mild reaction conditions. Notably, present proceeded efficiency transition-metal-catalyst-free key to success use 1,3-dicyanobenzene as a redox mediator visible-light irradiation, which effectively suppresses formation simple reduction, i.e., hydrodehalogenation, products afford desired in good yields. Mechanistic investigations proposed that reductive radical-polar crossover pathway likely be involved this transformation.

Язык: Английский

Процитировано

1

Synthesis of N-sulfenylimines via an electrochemical radical coupling of amines and thiols mediated by bromide ions DOI
Qian Wang, Haibo Mei, Romana Pajkert

и другие.

Tetrahedron, Год журнала: 2024, Номер 162, С. 134133 - 134133

Опубликована: Июль 3, 2024

Язык: Английский

Процитировано

1

Recent Advances in On‐line Mass Spectrometry Toolbox for Mechanistic Studies of Organic Electrochemical Reactions DOI
Kaixiang Chen, Qiongqiong Wan, Shiqi Wei

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер 30(57)

Опубликована: Июль 31, 2024

Electrochemical reactions are very complex and involve a variety of physicochemical processes. Accurate systematic monitoring intermediate process changes during the reaction is essential for understanding mechanism electrochemical basis rational design new reactions. On-line analysis based on mass spectrometry (MS) has become an important tool studying This technique different ionization sampling means realizes on-line by establishing electrochemistry-MS (EC-MS) coupling devices. In particular, it provides key evidence elucidating capturing identifying reactive intermediates. review will categorize various EC-MS devices organic systems they study, highlighting latest research progress in recent years. It also analyze properties look forward to future development EC-MS.

Язык: Английский

Процитировано

1