Selective Synthesis of 3-Selenoindoles via Selenation of Indoles under Catalyst-Free Condition DOI

Dengpeng Xia,

Qi Wu, Zhihua Cai

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(1), P. 349 - 349

Published: Jan. 1, 2025

Language: Английский

Alkene versus alkyne reactivity in unactivated 1,6-enynes: regio- and chemoselective radical cyclization with chalcogens under metal- and oxidant-free conditions DOI
Mohana Reddy Mutra, Vishal Suresh Kudale, Jing Li

et al.

Green Chemistry, Journal Year: 2020, Volume and Issue: 22(7), P. 2288 - 2300

Published: Jan. 1, 2020

Substituted pyrrolidine derivatives are obtained via regio- and chemoselective 5-exo-dig radical cyclization of unactivated 1,6-enynes with chalcogens under metal- oxidant-free conditions.

Language: Английский

Citations

83

Visible photons as ideal reagents for the activation of coloured organic compounds DOI Creative Commons
Lorenzo Di Terlizzi, Luca Nicchio,

Stefano Protti

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(10), P. 4926 - 4975

Published: Jan. 1, 2024

In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.

Language: Английский

Citations

13

Iodine-Catalyzed Selenylation of 2H-Indazole DOI
Amrita Dey, Alakananda Hajra

The Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 84(22), P. 14904 - 14910

Published: Oct. 16, 2019

A metal-free, environmentally friendly protocol for the arylselenylation of 2H-indazole has been developed using a catalytic amount I2 under ambient conditions. number 3-(phenylselanyl)-2H-indazoles with wide functional group tolerance have synthesized in good yields at room temperature. Mechanistic studies suggest that reaction possibly proceeds through an ionic pathway.

Language: Английский

Citations

57

Metal- and photocatalyst-free synthesis of 3-selenylindoles and asymmetric diarylselenides promoted by visible light DOI Creative Commons
Ignacio D. Lemir, Willber D. Castro‐Godoy, Adrián A. Heredia

et al.

RSC Advances, Journal Year: 2019, Volume and Issue: 9(39), P. 22685 - 22694

Published: Jan. 1, 2019

A novel and sustainable procedure was developed for the synthesis of 3-selenylindoles employing diorganyl diselenides indoles or electron-rich arenes as starting materials. Visible blue light used to promote reaction without transition metal complexes organic photocatalysts sensitizers. Additives such strong oxidants bases were not required. Moreover, ethanol employed a benign solvent under mild conditions. Through this easy eco-friendly approach, several number asymmetric diarylselenides obtained in good excellent isolated yields.

Language: Английский

Citations

56

Light‐Mediated Seleno‐Functionalization of Organic Molecules: Recent Advances DOI
Jamal Rafique, Daniel S. Rampon, Juliano B. Azeredo

et al.

The Chemical Record, Journal Year: 2021, Volume and Issue: 21(10), P. 2739 - 2761

Published: March 3, 2021

Organoselenium compounds constitute an important class of substances with applications in the biological, medicinal and material sciences as well modern organic synthesis, attracting considerable attention from scientific community. Therefore, construction C-Se bond via facile, efficient sustainable strategies to access complex scaffolds simple substrates are appealing hot topic. Visible light can be regarded alternative source energy is associated environmentally-friendly processes. Recently, use visible-light mediated seleno-functionalization has emerged ideal powerful route obtain high-value selenylated products, diminished cost waste. This approach, involving photo-excited substrates/catalyst single-electron transfer (SET) between presence visible been successfully used versatile direct insertion organoselenium moieties activated unactivated C(sp3 )-H, C(sp2 C(sp)-H bonds C-heteroatom bonds. In most cases, ease operation accessibility (LEDs or commercial CFL bulbs) makes this approach more attractive than traditional strategies.

Language: Английский

Citations

44

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry DOI Creative Commons
Juliano B. Azeredo, Filipe Penteado, Vanessa Nascimento

et al.

Molecules, Journal Year: 2022, Volume and Issue: 27(5), P. 1597 - 1597

Published: Feb. 28, 2022

Organoselenium compounds have been successfully applied in biological, medicinal and material sciences, as well a powerful tool for modern organic synthesis, attracting the attention of scientific community. This great success is mainly due to breaking paradigm demonstrated by innumerous works, that selenium were toxic would potential impact on environment. In this update review, we highlight relevance these several fields research possibility synthesize them through more environmentally sustainable methodologies, involving catalytic processes, flow chemistry, electrosynthesis, use alternative energy sources, including mechanochemical, photochemistry, sonochemical microwave irradiation.

Language: Английский

Citations

37

Visible Light-Mediated C(sp2)–H Selenylation of Amino Pyrazole and Amino Uracils in the Presence of Rose Bengal as an Organophotocatalyst DOI
Danish Ali, Tasneem Parvin, Lokman H. Choudhury

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(2), P. 1230 - 1239

Published: Jan. 7, 2022

Herein, we report an efficient methodology for the synthesis of alkyl, benzyl, and phenyl selenoethers aminopyrazoles aminouracils by C(sp2)-H functionalization in presence visible light Rose Bengal as organophotocatalyst. The reaction amino pyrazole/iosothiazole/isoxazole or uracils with 0.5 equivalent diphenyl/dibenzyl/diethyl diselenides acetonitrile medium a catalytic amount provided corresponding phenyl, ethyl good to very yields. We have also utilized some selenylated preparation pyrazole-fused dihydropyrimidines tethered arylselenoethers catalyst-free one-pot three-component reaction. notable features this are metal-free conditions, yields, use organic photocatalyst, wide substrate scope; it is applicable gram-scale provides medicinally important heterocycles such amio-pyrazole, isoxazole, isothiazole, uracils.

Language: Английский

Citations

34

Recent Advances in Light-Induced Selenylation DOI Creative Commons
Stefano Protti, Maurizio Fagnoni

ACS Organic & Inorganic Au, Journal Year: 2022, Volume and Issue: 2(6), P. 455 - 463

Published: Aug. 19, 2022

Selenium-containing organic molecules have recently found a plethora of applications, ranging from synthesis to pharmacology and material sciences. In view these concepts, the development mild, efficient, general protocols for formation C–Se bonds is desirable, light induced approaches are appealing ways. The aim this Review provide reader with most recent examples promoted selenylation processes.

Language: Английский

Citations

31

Blue Light Irradiated Metal-, Oxidant-, and Base-Free Cross-Dehydrogenative Coupling of C(sp2)–H and N–H Bonds: Amination of Naphthoquinones with Amines DOI
Raushan Kumar Jha, Monojit Batabyal, Sangit Kumar

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7401 - 7424

Published: May 12, 2023

Herein, we report a blue-light-driven amination of C(sp2)-H bond naphthoquinones and quinones with the N-H primary secondary amines for synthesis 2-amino-naphthoquinones 2-amino-quinones. The coupling wide array aliphatic, aromatic, chiral, primary, having electron donating (-CH3, -OCH3, -SCH3), withdrawing (-F, -Cl, -Br, -I), CO2H, -OH, -NH2 groups acidic protons selectively occurred to afford C-N coupled in 60-99% yields hydrogen gas as byproduct methanol solvent without using any additional reagents, additives, oxidant under blue light irradiation. Mechanistic insight by DFT computation, controlled experiments, kinetic isotopic effect, substitution effect substrates suggest that reaction proceeds radical pathway which naphthoquinone forms highly oxidizing naphthoquinonyl biradical upon irradiation (457 nm). Consequently, transfer from electron-rich amine an leads anion aminyl cation, followed proton delocalization leading carbon-centered radical. cross-coupling nitrogen radicals bond, subsequent elimination (which was also confirmed GC-TCD), affording 2-amino-1,4-naphthoquinone metal-, reagent-, base-, oxidant-free conditions.

Language: Английский

Citations

22

Synthetic strategies for aryl/heterocyclic selenides and tellurides under transition-metal-catalyst free conditions DOI Creative Commons
Debasish Kundu

RSC Advances, Journal Year: 2021, Volume and Issue: 11(12), P. 6682 - 6698

Published: Jan. 1, 2021

Aryl and heteroaryl selenides tellurides are found to have broad applications in the diverse fields such as medicine, biology, materials science, pharmaceutical etc. thus their synthesis remains a challenging field for synthetic chemists last decade. Although large no of methodologies been developed based on metal catalyzed C-Se/Te coupling, number researches has focused developing catalyst free protocols due sustainability recent times. This review covers all developments decade under conditions by using different sustainable techniques e.g. greener reagents solvents, ball milling, visible light photocatalysis, microwave, ultrasound

Language: Английский

Citations

39