Pnictogen bonding enabled photosynthesis of chiral selenium-containing pyridines from pyridylphosphonium salts DOI Creative Commons
Qiang Liu, Beibei Zhang, Chaoshen Zhang

et al.

Fundamental Research, Journal Year: 2023, Volume and Issue: 5(2), P. 654 - 662

Published: April 20, 2023

Pyridylphosphonium salts, which are readily available and air thermally stable, have been used to effectively synthesize structurally diverse pyridines. Herein, we report the pnictogen bonding (PnB) enabled photoactivation of pyridylphosphonium salts with catalytic potassium carbonate generate pyridyl radical for pyridine synthesis. Remarkably, this light-driven transformation allowed chiral pool synthesis excellent chirality retention, giving a wide range selenium-containing On basis our combined computational experimental studies, propose that PnB between enables access photoactive charge transfer complex, is able undergo single electron its transformation.

Language: Английский

Recent Developments in the Photochemical Synthesis of Functionalized Imidazopyridines DOI Creative Commons
Christine Tran, Abdallah Hamzé

Molecules, Journal Year: 2022, Volume and Issue: 27(11), P. 3461 - 3461

Published: May 27, 2022

Imidazopyridines constitute one of the most important scaffolds in medicinal chemistry, as their skeleton could be found a myriad biologically active molecules. Although numerous strategies were elaborated for imidazopyridine preparation 2010s, novel eco-compatible synthetic approaches have emerged, conscious climate change concerns. In this framework, photochemical methods been promoted to conceive heterocyclic motif over last decade. This review covers recently published works on synthesizing highly functionalized imidazopyridines by light induction.

Language: Английский

Citations

22

Urea Hydrogen Peroxide and Ethyl Lactate, an Eco-Friendly Combo System in the Direct C(sp2)–H Bond Selenylation of Imidazo[2,1-b]thiazole and Related Structures DOI Creative Commons
Cassio A. O. Moraes,

Rafaely B. C. Santos,

Marcos F. O. Cavalcante

et al.

ACS Omega, Journal Year: 2023, Volume and Issue: 8(42), P. 39535 - 39545

Published: Oct. 12, 2023

Herein, we describe a urea hydrogen peroxide-mediated sustainable protocol for the synthesis of selenylated imidazo[2,1-b]thiazole by using half molar equivalent diorganyl diselenides in ethyl lactate as greener solvent. The reaction features high yields, easy performance on gram scale, metal-free conditions, well applicability to imidazopyridine and imidazopyrimidine.

Language: Английский

Citations

11

Silver-catalyzed direct selanylation of indoles: synthesis and mechanistic insights DOI Creative Commons
Elise Ane Maluf Rios,

Carla M. B. Gomes,

Gabriel L. Silvério

et al.

RSC Advances, Journal Year: 2023, Volume and Issue: 13(2), P. 914 - 925

Published: Jan. 1, 2023

Herein we describe the Ag(i)-catalyzed direct selanylation of indoles with diorganoyl diselenides. The reaction gave 3-selanylindoles high regioselectivity and also allowed access to 2-selanylindoles when C3 position indole ring was blocked

Language: Английский

Citations

10

Catalytic Antioxidant Activity of Bis-Aniline-Derived Diselenides as GPx Mimics DOI Creative Commons
Giancarlo V. Botteselle, Welman C. Elias, Luana Bettanin

et al.

Molecules, Journal Year: 2021, Volume and Issue: 26(15), P. 4446 - 4446

Published: July 23, 2021

Herein, we describe a simple and efficient route to access aniline-derived diselenides evaluate their antioxidant/GPx-mimetic properties. The were obtained in good yields via ipso-substitution/reduction from the readily available 2-nitroaromatic halides (Cl, Br, I). These present GPx-mimetic properties, showing better antioxidant activity than standard compounds, ebselen diphenyl diselenide. DFT analysis demonstrated that electronic properties of substituents determine charge delocalization partial on selenium, which correlate with catalytic performances. amino group concurs stabilization selenolate intermediate through hydrogen bond selenium.

Language: Английский

Citations

23

Oxone® Mediated Regioselective C(sp2)−H Selenylation and Thiocyanation of Pyrazolo[1,5‐a]pyrimidines at Room Temperature DOI

Abhinay S. Chillal,

Rajesh T. Bhawale,

Umesh A. Kshirsagar

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(1)

Published: Jan. 2, 2024

Abstract A mild Oxone® mediated reaction for direct regioselective C−H selenylation and thiocyanation of pyrazolo[1,5‐ a ]pyrimidines is established at ambient temperature. This practical efficient methodology employs as user friendly, green, non‐toxic cheap reagent to facilitate room The present method offers high regioselectivity, broad substrate scope, conditions excellent yields. Further, this eco‐friendly approach could easily be extended other heterocycles. Mechanistic studies indicate that the occurs through electrophilic substitution mechanism via generation an chalcogen species.

Language: Английский

Citations

3

A sustainable approach for the bis-selenylation of alkynes: Design, synthesis and mechanistic studies DOI
Lucas Martins Correa Böhs,

Calebe Hebrom Livistom Silva,

Natália Emanuele Biolosor Kuntz

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155504 - 155504

Published: Feb. 1, 2025

Language: Английский

Citations

0

Catalyst- and metal-free C(sp2)–H bond selenylation of (N-hetero)-arenes using diselenides and trichloroisocyanuric acid at room temperature DOI Creative Commons
José S. S. Neto, Isis Juliane Arantes Granja, Marcos R. Scheide

et al.

Scientific Reports, Journal Year: 2023, Volume and Issue: 13(1)

Published: Aug. 31, 2023

In this paper, we report an eco-friendly approach for the C(sp2)-H bond selenylation of imidazopyridines and other N-heteroarenes as well simple arenes at ambient temperature. This new protocol consists reaction between (N-hetero)-arenes diorganyl-diselenides trichloroisocyanuric acid (TCCA)-ethanol reagent system. a short time, desired selenylated products were obtained regioselectively in good yields, with tolerance wide range functional groups.

Language: Английский

Citations

8

Lighting Up the Organochalcogen Synthesis: A Concise Update of Recent Photocatalyzed Approaches DOI Open Access
Ricardo H. Bartz,

Luiz H. Dapper,

Jean C. Kazmierczak

et al.

Catalysts, Journal Year: 2023, Volume and Issue: 13(3), P. 520 - 520

Published: March 3, 2023

This review describes the recent advances in photocatalyzed reactions to form new carbon–sulfur and carbon–selenium bonds. With a total of 136 references, which 81 articles are presented, authors introduce five sections an updated picture state art light-promoted synthesis organochalcogen compounds (from 2019 present). The sulfides by direct sulfenylation C–C π-bonds; sulfones; activation Csp2–N bond formation Csp2–S bonds; thiol ester, thioether thioacetal; organoselenium discussed, with detailed reaction conditions selected examples for each protocol.

Language: Английский

Citations

7

Recent Advances in the Use of Diorganyl Diselenides as Versatile Catalysts DOI Creative Commons
Gabriel P. Costa, Gustavo B. Blödorn, Angelita M. Barcellos

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(18), P. 6614 - 6614

Published: Sept. 14, 2023

The importance of organoselenium compounds has been increasing in synthetic chemistry. These reagents are well-known as electrophiles and nucleophiles many organic transformations, recent years, their functionality catalysts also largely explored. interest organoselenium-based is due to high efficacy, mild reaction conditions, strong functional compatibility, great selectivity. Allied catalysts, the use inorganic oxidants that act by regenerating catalytic species for pathway common. Here, we provide a comprehensive review last five years transformations promoted diorganyl diselenide selenium-based catalyst. This report divided into four sections: (1) cyclisation reactions, (2) addition reactions oxidative functionalisation, (3) oxidation reduction (4) involving phosphorus-containing starting materials.

Language: Английский

Citations

7

Electrochemical Regioselective C(sp2)-H Bond Chalcogenation of Pyrazolo[1,5-a]pyrimidines via Radical Cross Coupling at Room Temperature DOI Creative Commons

Abhinay S. Chillal,

Rajesh T. Bhawale,

Siddharth Sharma

et al.

Published: April 9, 2024

In this report, we disclose an electrochemical approach for the C(sp2)-H chalcogenation of pyrazolo[1,5-a]pyrimidines at room temperature via radical cross-coupling reaction. The reaction takes place within undivided cell employing graphite electrodes, with TBABF4 acting as supporting electrolyte. This technique offers a rapid, oxidant-free, and environmentally conscious protocol achieving regioselective specifically C3 position pyrazolo[1,5-a]pyrimidines. Furthermore, procedure uses only 0.5 equivalents diaryl chalcogenides which underscores atom economy protocol. Key attributes methodology include mild conditions, short time, utilization cost-effective electrode materials, reliable achievement yields ranging from good to excellent friendly conditions. Cyclic voltammetry studies quenching experiments suggest pathway mechanism.

Language: Английский

Citations

2