Mechanochemical Solvent‐Free One‐Pot Synthesis of Poly‐Functionalized 5‐(Arylselanyl)‐1H‐1,2,3‐triazoles Through a Copper(I)‐Catalyzed Click Reaction DOI
Pintu Karmakar, Indrajit Karmakar, Debojyoti Mukherjee

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(63)

Published: Sept. 4, 2023

A mechanochemistry-driven practical and efficient synthetic protocol for accessing diverse series of biologically relevant poly-functionalized 5-(arylselanyl)-1H-1,2,3-triazoles through copper(I)-catalyzed click reaction between aryl/heteroaryl acetylenes, diaryl diselenides, benzyl bromides, sodium azide has been accomplished under high-speed ball-milling. Advantages this method include operational simplicity, avoidance using solvent external heating, one-pot synthesis, short time in minutes, good to excellent yields, broad substrate scope, gram-scale applications. Furthermore, synthesized organoselenium compounds were synthetically diversified promising selenones.

Language: Английский

Recent progress in the electrochemical selenofunctionalization of alkenes and alkynes DOI
Pei Qu,

You‐Qin Jiang,

Yong‐Hao Wang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(19), P. 7485 - 7507

Published: Jan. 1, 2023

The recent advances on the electrochemical selenofunctionalization of unsaturated C–C bonds were comprehensively summarized in this review.

Language: Английский

Citations

32

Electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens involving C–S/Se bond formation DOI
Jianchao Liu, Jie‐Ping Wan, Yunyun Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(2), P. 597 - 630

Published: Nov. 23, 2023

This review highlights the recent progress in electrochemical difunctionalization of alkenes and alkynes involving C–S/Se bond formation to access organochalcogen frameworks.

Language: Английский

Citations

30

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

23

Regio- and Stereoselective Synthesis of 3-Selenylazaflavanones and 3-Selenylflavanones via Electrochemically Facilitated Selenylation Cascade DOI

Shaogao Zeng,

Yong Zeng, Hui Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 4074 - 4084

Published: Feb. 23, 2024

Herein, an oxidant- and metal-free electrochemical selenylation reaction of chalcones with diselenides for the synthesis 3-selenylazaflavanones 3-selenylflavanones at room temperature was reported. The method proceeded under mild conditions, exhibited a broad substrate scope, provided selenylated products in moderate to excellent yields high regio- stereoselectivity. could also be readily scaled up efficiency. Detailed mechanistic studies through control experiments disclosed that selenium-based radical might participate this transformation.

Language: Английский

Citations

10

Electrochemical Multicomponent Cascade Radical Process Enabling Synthesis of Iodomethyl Spiropyrrolidinyl‐Oxindoles DOI

Jingrui He,

Haibo Mei, Jorge Escorihuela

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(15), P. 1691 - 1698

Published: March 19, 2024

Comprehensive Summary A novel electrochemical multicomponent cascade reaction of indole‐tethered alkenes with CF 3 SO 2 Na and n ‐Bu 4 NI has been developed, which enables the rapid assembly spiropyrrolidinyl‐oxindoles in good yields. The experimental results DFT calculations suggest that this proceeds through oxidation Na, radical coupling alkene, spirocyclization, sulfinate, iodide substitution, water coupling. This strategy features mild conditions, easy‐to‐handle reactants, chemical finding not only enriches research contents but also provides a green for construction compared existing methodologies.

Language: Английский

Citations

9

Electrochemical Regioselective C(sp2)–H Selenylation and Sulfenylation of Substituted 2-Amino-1,4-naphthoquinones DOI
Pintu Karmakar, Indrajit Karmakar, D. R. PAL

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(2), P. 1049 - 1060

Published: Jan. 4, 2023

A straightforward and efficient electrochemical method for regioselective C(sp2)-H selenylation sulfenylation of substituted 2-amino-1,4-naphthoquinones has been unearthed. This oxidative cross-coupling reaction avoids using transition metal catalysts, oxidants, high temperatures. The other notable advantages this protocol are the tolerance diverse functional groups, mild conditions at ambient temperature, energy efficiency, good to excellent yields, short times (in minutes), gram-scale applicability, eco-friendliness.

Language: Английский

Citations

22

Versatile electrooxidative amino- and oxyselenation of alkenes DOI
R. Wang,

Nana Zhang,

Yonghong Zhang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(10), P. 3925 - 3930

Published: Jan. 1, 2023

We herein describe a methodology for the production of organoselenium compounds by electrocatalytic difunctionalisation alkenes.

Language: Английский

Citations

20

Photo-induced cyclization of olefinic amides towards sulfonamidylated iminoisobenzofurans and benzoxazines DOI
Changduo Pan,

Shipeng Luo,

Yechun Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(14), P. 3479 - 3484

Published: Jan. 1, 2023

A visible-light induced radical cyclization of olefinic amides with easily available N -sulfonylaminopyridinium salts towards iminoisobenzofurans and benzoxazines has been developed.

Language: Английский

Citations

16

Chemoselective electrochemical seleno-cyclization of dienes to medium-sized benzo[b]azocines DOI

Zhichuan Wang,

Xin Wang, Q. Li

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 109058 - 109058

Published: Sept. 10, 2023

Language: Английский

Citations

15

Electrophotocatalysis Versus Indirect Electrolysis: Electrochemical Selenocyclization of 3‐Aza‐1,5‐dienes Facilitated by Energy Transfer, Direct Photolysis or N‐Hydroxyphthalimide DOI

Dongyin Wang,

Li Zeng, Jifu Shi

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(36)

Published: April 23, 2024

Three hybrid electrochemical protocols, which involve the energy transfer, direct photolysis and N-hydroxyphthalimide catalyst, respectively, are presented for selenylation/cyclization of fragile substrates 3-aza-1,5-dienes with diorganyl diselenides to afford 3-selenomethyl-4-pyrrolin-2-ones. The two electrophotocatalytic reactions indirect electrolysis one both regioselective external-oxidant- transition-metal-free, associated a broad substrate scope high Se-economy, all three methods amenable gram-scale syntheses, late-stage functionalizations, sunlight-induced experiments all-solar-driven syntheses.

Language: Английский

Citations

6