Synthesis of Bibenzyl Derivatives via Visible-Light-Promoted 1,5-Hydrogen Atom Transfer/Radical Coupling Reactions of N-Fluorocarboxamides DOI Open Access

Panpan Lei,

Qinlin Chen,

Hang Chen

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(1), P. 254 - 254

Published: Jan. 1, 2023

Visible light-mediated 1,5-hydrogen atom transfer and radical coupling reactions have been accomplished using N-fluoro-substituted benzamides.This method exhibits a broad substrate scope high functional group tolerance, giving the corresponding bibenzyl products with generally good yields.Furthermore, this strategy could also be used to aliphatic amides.

Language: Английский

Electrochemical enaminone C–H thiolation/C–N amination cascade for thiazole synthesis and its diastereoselective dearomatization DOI
Haijin Guo, Yunyun Liu, Chengping Wen

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(13), P. 5058 - 5063

Published: Jan. 1, 2022

The electrochemical annulation of enaminones/analogous enamines and thioureas providing 2-aminothiazoles has been realized. Modulating the electrolyte enables diastereoselective synthesis 4,5-dialkoxyl thiazolines by dearomatization.

Language: Английский

Citations

64
Electrochemical oxidative cross coupling of NH-sulfoximines with disulfides DOI
Shuai Zhang, Meiqian Hu, Changsheng Qin

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(6), P. 2576 - 2583

Published: Jan. 1, 2024

An electrochemical method for thioetherification of NH-sulfoximines with disulfides is reported. The utilization electrochemistry facilitating these reactions eliminates the necessity external oxidants, bases, and metal catalysts.

Language: Английский

Citations

11
(CoFeMnCuNiCr)3O4 High-Entropy Oxide Nanoparticles Immobilized on Reduced Graphene Oxide as Heterogeneous Catalysts for Solvent-Free Aerobic Oxidation of Benzyl Alcohol DOI
Seyedsaeed Mehrabi-Kalajahi, Ahmad Ostovari Moghaddam, Fahimeh Hadavimoghaddam

et al.

ACS Applied Nano Materials, Journal Year: 2024, Volume and Issue: 7(5), P. 5513 - 5524

Published: Feb. 21, 2024

The development of noble metal-free heterogeneous catalysts holds promise for the solvent-free and selective aerobic oxidation organic compounds. However, moderate activity these under atmospheric conditions limits their industrial use. In this work, synthesis (CoFeMnCuNiCr)3O4 high-entropy oxide (HEO) nanoparticles grafting on reduced graphene (rGO) to produce a HEO–rGO nanocomposite is detailed. X-ray diffraction (XRD), scanning electron microscopy (SEM), Raman Mössbauer spectroscopy analyses confirm formation spinel HEO phase. nanocomposites are used benzyl alcohol, displaying excellent catalytic performance. Up 10.36% conversion 78.5% selectivity benzaldehyde can be achieved in only 4 h. An extensive analytical study shows that performance attributed synergistic effect between rGO active sites abundant oxygen vacancies within nanoparticles. Moreover, four robust machine learning models including Adaptive Boosting (AdaBoost), Categorical (CatBoost), Random Forest (RF), eXtreme Gradient (XGBoost) applied predict reactions. XGBoost demonstrated as best-fitting model all data with an error less than 2.5%. Overall, both experimental numerical suggest potential application chemical industries alcohols added-value products.

Language: Английский

Citations

11
Electrochemical N(sp2)–H/C(sp3)–H cross-coupling reaction between sulfoximines and alkylarenes DOI

Qing‐Ru Zhu,

Peng-Zhan Zhang,

Xiang Sun

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(10), P. 5824 - 5831

Published: Jan. 1, 2024

An electrochemical oxidation-induced amination of simple alkylarenes with sulfoximines as a nitrogen source and 5,6-dimethyl-1 H -benzo[ d ]imidazole catalyst was developed.

Language: Английский

Citations

7
Remote C(sp3)–H heteroarylation of N-fluorocarboxamides with quinoxalin-2(1H)-ones under visible-light-induced photocatalyst-free conditions DOI

Liangming Xuan,

Ruyang Du,

Panpan Lei

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(24), P. 9475 - 9481

Published: Jan. 1, 2022

A photocatalyst-free visible-light-promoted remote C(sp 3 )–H heteroarylation of N -fluoroamides with quinoxalin-2(1 H )-ones was developed. All types δ-C(sp bonds in the could be site-specific activated through 1,5-HAT process.

Language: Английский

Citations

26
NHPI-Mediated Electrochemical α-Oxygenation of Amides to Benzimides DOI
Fang Bai, Ning Wang,

Yinshan Bai

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(5), P. 2985 - 2998

Published: Feb. 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.

Language: Английский

Citations

11
Electrochemical oxidation-induced benzylic C(sp3)–H functionalization towards the atom-economic synthesis of oxazole heterocycles DOI
Na Yang, Anni Li, Hui Gao

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(13), P. 5128 - 5133

Published: Jan. 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.

Language: Английский

Citations

11
Visible-light-driven intramolecular xanthylation of remote unactivated C(sp3)-H bonds DOI Creative Commons
Hang Chen, Yang Zhou,

Panpan Lei

et al.

Green Synthesis and Catalysis, Journal Year: 2022, Volume and Issue: 4(4), P. 350 - 354

Published: July 16, 2022

Visible light-mediated site-specific C(sp3)-H xanthylation of amides has been accomplished using N-xanthylamides. The N-centered radicals generated by light initiation N-xanthylamide substrates undergo 1,5-hydrogen atom transfer to form benzylic or alkyl radical intermediates under metal- and catalyst-free conditions. This method exhibits a broad substrate scope, high functional group tolerance, regioselectivity. Furthermore, this strategy provides straightforward access range derivatives through the subsequent elaboration xanthate group.

Language: Английский

Citations

18
Selective Electrochemical Halogenation of Functionalized Quinolone DOI
Meiqian Hu, Shuai Zhang, Changsheng Qin

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(18), P. 12958 - 12970

Published: Aug. 24, 2023

This work describes an effective C3–H halogenation of quinoline-4(1H)-ones under electrochemical conditions, in which potassium halides serve as both halogenating agents and electrolytes. The protocol provides expedient access to different halogenated with unique regioselectivity, broad substrate scope, gram-scale synthesis employing convenient, environmentally friendly electrolysis, undivided cell. Mechanism studies have shown that halogen radicals can promote the activation N–H bonds quinolones.

Language: Английский

Citations

10
Recent advances in electrochemical C–H bond amination DOI
Chen Liu, Ji‐Xuan Liu, Wenyi Li

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(20), P. 5309 - 5330

Published: Jan. 1, 2023

.This review summarizes recent developments in electrochemical C–H amination, highlighting key inspirations and proposed mechanisms behind these sustainable oxidation-free approaches for constructing C–N bonds directly from bonds.

Language: Английский

Citations

10