» Articles » PMID: 35519497

Metal- and Photocatalyst-free Synthesis of 3-selenylindoles and Asymmetric Diarylselenides Promoted by Visible Light

Overview
Journal RSC Adv
Specialty Chemistry
Date 2022 May 6
PMID 35519497
Authors
Affiliations
Soon will be listed here.
Abstract

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

Citing Articles

Bismuth(III)-Catalyzed Regioselective Selenation of Indoles with Diaryl Diselenides: Synthesis of 3-Selanylindoles.

Matsumura M, Umeda A, Sumi Y, Aiba N, Murata Y, Yasuike S Molecules. 2024; 29(13).

PMID: 38999179 PMC: 11243167. DOI: 10.3390/molecules29133227.


Dimsyl Anion Enables Visible-Light-Promoted Charge Transfer in Cross-Coupling Reactions of Aryl Halides.

Pan L, Cooke M, Spencer A, Laulhe S Adv Synth Catal. 2023; 364(2):420-425.

PMID: 37197314 PMC: 10187771. DOI: 10.1002/adsc.202101052.


A diselenide additive enables photocatalytic hydroalkoxylation of -difluoroalkenes.

Herrick R, Abd El-Gaber M, Coy G, Altman R Chem Commun (Camb). 2023; 59(37):5623-5626.

PMID: 37082905 PMC: 10164105. DOI: 10.1039/d3cc01012k.


Recent Advances in Light-Induced Selenylation.

Protti S, Fagnoni M ACS Org Inorg Au. 2023; 2(6):455-463.

PMID: 36855533 PMC: 9955339. DOI: 10.1021/acsorginorgau.2c00033.


Synthesis and Application Dichalcogenides as Radical Reagents with Photochemical Technology.

Wang C, Zhang Y, Sun K, Yu T, Liu F, Wang X Molecules. 2023; 28(4).

PMID: 36838986 PMC: 9963440. DOI: 10.3390/molecules28041998.


References
1.
Alves F, Barreiro E, Fraga C . From nature to drug discovery: the indole scaffold as a 'privileged structure'. Mini Rev Med Chem. 2009; 9(7):782-93. DOI: 10.2174/138955709788452649. View

2.
Vasquez-Cespedes S, Ferry A, Candish L, Glorius F . Heterogeneously catalyzed direct C-H thiolation of heteroarenes. Angew Chem Int Ed Engl. 2015; 54(19):5772-6. DOI: 10.1002/anie.201411997. View

3.
Du Y, Pearson R, Lim C, Sartor S, Ryan M, Yang H . Strongly Reducing, Visible-Light Organic Photoredox Catalysts as Sustainable Alternatives to Precious Metals. Chemistry. 2017; 23(46):10962-10968. PMC: 5941304. DOI: 10.1002/chem.201702926. View

4.
Nogueira C, Zeni G, Rocha J . Organoselenium and organotellurium compounds: toxicology and pharmacology. Chem Rev. 2004; 104(12):6255-85. DOI: 10.1021/cr0406559. View

5.
Chen Y, Cho C, Shi F, Larock R . Synthesis of 3-sulfenyl- and 3-selenylindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal alkynes, followed by n-Bu(4)NI-induced electrophilic cyclization. J Org Chem. 2009; 74(17):6802-11. PMC: 2735226. DOI: 10.1021/jo9014003. View