Electrochemical NiH‐Catalyzed C(sp3)−C(sp3) Coupling of Alkyl Halides and Alkyl Alkenes DOI Open Access
Pengfei Li,

Guangsheng Kou,

Tian Feng

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(44)

Published: Sept. 14, 2023

Abstract Herein, an electrochemically driven NiH‐catalyzed reductive coupling of alkyl halides and alkenes for the construction C sp 3 −C bonds is firstly reported. Notably, serve dual function as substrates hydrogen sources to generate NiH species under electrochemical conditions. The tunable nature this reaction realized by introducing intramolecular coordinating group substrate, where product can be easily adjusted give desired branched products. method proceeds mild conditions, exhibits a broad substrate scope, affords moderate excellent yields with over 70 examples, including late‐stage modification natural products drug derivatives. Mechanistic insights offer evidence process. ‐carbon‐halogen activated through single electron transfer (SET) nickel catalyst in its low valence state, generated cathodic reduction, generation from pivotal transformation.

Language: Английский

Organo‐Mediator Enabled Electrochemical Deuteration of Styrenes DOI

Keming Yang,

Tian Feng, Youai Qiu

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(45)

Published: Sept. 12, 2023

Despite widespread use of the deuterium isotope effect, selective labeling chemical molecules remains a major challenge. Herein, facile and general electrochemically driven, organic mediator enabled deuteration styrenes with oxide (D2 O) as economical source was reported. Importantly, this transformation could be suitable for various electron rich mediated by triphenylphosphine (TPP). The reaction proceeded under mild conditions without transition-metal catalysts, affording desired products in good yields excellent D-incorporation (D-inc, up to >99 %). Mechanistic investigations means experiments cyclic voltammetry tests provided sufficient support transformation. Notably, method proved powerful tool late-stage biorelevant compounds.

Language: Английский

Citations

48
Electrochemical NiH‐Catalyzed C(sp3)−C(sp3) Coupling of Alkyl Halides and Alkyl Alkenes DOI Open Access
Pengfei Li,

Guangsheng Kou,

Tian Feng

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(44)

Published: Sept. 14, 2023

Herein, an electrochemically driven NiH-catalyzed reductive coupling of alkyl halides and alkenes for the construction Csp3 -Csp3 bonds is firstly reported. Notably, serve dual function as substrates hydrogen sources to generate NiH species under electrochemical conditions. The tunable nature this reaction realized by introducing intramolecular coordinating group substrate, where product can be easily adjusted give desired branched products. method proceeds mild conditions, exhibits a broad substrate scope, affords moderate excellent yields with over 70 examples, including late-stage modification natural products drug derivatives. Mechanistic insights offer evidence process. sp3 -carbon-halogen activated through single electron transfer (SET) nickel catalyst in its low valence state, generated cathodic reduction, generation from pivotal transformation.

Language: Английский

Citations

24
Electroreductive deuteroarylation of alkenes enabled by an organo-mediator DOI Creative Commons
Xinling Li, Jianfeng Zhou,

Weijie Deng

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(29), P. 11418 - 11427

Published: Jan. 1, 2024

An environmentally friendly electroreduction approach is disclosed for site-specific introduction of deuterium via anti-Markovnikov selective deuteroarylation alkenes and aryl iodides with bipyridine as a mediator D 2 O ‘D’ source.

Language: Английский

Citations

8
Organo-mediator enabled electrochemical transformations DOI
Wei-Mei Zeng, Yanwei Wang,

Chunhui Peng

et al.

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review highlights organo-mediators that enable electrochemical reactions via outer-sphere electron transfer (ET), offering advantages such as availability, tunability, and simplified post-processing compared to direct electrolysis.

Language: Английский

Citations

1
Recent Advances in Electrochemical Cascade Cyclization Reactions DOI
Cai Zhang, Yunyun Liu,

Demao Chen

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(18), P. 2911 - 2925

Published: Feb. 20, 2023

Abstract This review highlights recent progress in electrochemical cascade cyclization reactions for the synthesis of carbon rings and heterocycles, such as pyridines, quinolines, phenanthridines, cinnolines, 1,4-dihydroquinolines, oxindoles, imidazo[1,5-α]pyridines, imidazoles, etc. The works included herein are introduced two major sections heterocycle construction carbocycle reactions, covering reported from 2012 to 2022. 1 Introduction 2 Electrochemical Cascade Cyclization Synthesis Heterocycles 2.1 Pyridines, Quinolines, Phenanthridines, Cinnolines 2.2 1,4-Dihydroquinolines, Hexacyclic Sulfonamides, Thiazines 2.3 Hydroisoquinolinones Hydroquinolinones 2.4 Quinazolin-4(3H)-ones 2.5 4H-3,1-Benzoxazines 2.6 Oxindoles 2.7 Indolines Indoles 2.8 Imidazo[1,5-α]pyridines Imidazoles 2.9 Imidazolones, Imidazolidinones, Oxazolones, Oxazolidinones 2.10 Benzoxazoles, Oxazolines, Isoxazolines 2.11 Furans Dihydrofurans 2.12 Indolizines, Pyrazoles, Triazolium Inner Salts 2.13 Sulfonated Benzothiophenes, Thiazoles, Dihydrothiazoles, 1,3,4-Thiadiazoles 2.14 Lactones 3 Construction Carbocycles 3.1 Carbon Polycycles Spiroindenes 3.2 Difluoroacyl (Hetero)arenes Indenones 4 Conclusion

Language: Английский

Citations

22
Metal-free electrochemical dihydroxylation of unactivated alkenes DOI Creative Commons
Min Liu, Tian Feng, Yanwei Wang

et al.

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: Oct. 13, 2023

Herein, a metal-free electrochemical dihydroxylation of unactivated alkenes is described. The transformation proceeds smoothly under mild conditions with broad range alkenes, providing valuable and versatile dihydroxylated products in moderate to good yields without the addition costly transition metals stoichiometric amounts chemical oxidants. Moreover, this method can be applied natural pharmaceutical derivatives, further demonstrating its synthetic utility. Mechanistic studies have revealed that iodohydrin epoxide intermediate are formed during reaction process.

Language: Английский

Citations

22
Electroreductive Cross‐Electrophile Coupling of Aziridines and Aryl Bromides DOI

Guoqing Yang,

Yanwei Wang, Youai Qiu

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(36)

Published: April 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.

Language: Английский

Citations

18
Catalyst-free electrochemical SNAr of electron-rich fluoroarenes using carboxylic acids DOI Creative Commons

Anzai Shi,

Yaowen Liu,

Ranran Zhang

et al.

eScience, Journal Year: 2024, Volume and Issue: 4(5), P. 100255 - 100255

Published: March 15, 2024

Herein, an electrochemically driven catalyst-free nucleophilic aromatic substitution (SNAr) of electron-rich fluoroarenes with carboxylic acids as weak nucleophiles under mild conditions was reported. A series highly valuable ester derivatives were obtained in a direct and rapid way. This transformation features commercially available reagents exceptionally broad substrate scope good functional group tolerance, using cheap abundant electrodes completed within short reaction time. Gram-scale synthesis complex biorelevant compounds ligation further highlighted the potential utility methodology. The mechanistic investigations density theory (DFT) calculations verified feasibility proposed pathway this transformation.

Language: Английский

Citations

6
Electrochemical dual α,β-C(sp3)–H functionalization of cyclic N-aryl amines DOI
Tian Feng, Zile Zhu, Dongmei Zhang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(7), P. 2681 - 2689

Published: Jan. 1, 2023

Herein, a straightforward route for dual α,β-C(sp 3 )–H functionalized cyclic N -aryl amines using combination of electrocatalysis and iron catalysis is disclosed, setting the stage challenging multiple site selective C–H functionalization.

Language: Английский

Citations

16
Electrochemical Palladium‐Catalyzed Oxidative Carbonylation‐Cyclization of Enallenols DOI Creative Commons
Jianwei Zhang, Biswanath Das, Oscar Verho

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(49)

Published: Oct. 12, 2022

Herein, we report an electrochemical oxidative palladium-catalyzed carbonylation-carbocyclization of enallenols to afford γ-lactones and spirolactones, which proceeds with excellent chemoselectivity. Interestingly, electrocatalysis was found have accelerating effect on the rate tandem process, leading a more efficient reaction than that under chemical redox conditions.

Language: Английский

Citations

20