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Review
. 2022 Aug 19;2(6):455-463.
doi: 10.1021/acsorginorgau.2c00033. eCollection 2022 Dec 7.

Recent Advances in Light-Induced Selenylation

Stefano Protti  1 , Maurizio Fagnoni  1
Affiliations
Review

Recent Advances in Light-Induced Selenylation

Stefano Protti et al. ACS Org Inorg Au. .

Abstract

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

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Bioactive selenides and diselenides.
Scheme 1
Scheme 1. Main Photochemical/Photocatalyzed Strategies for Selenylation Reactions
Scheme 2
Scheme 2. Photocatalyzed Preparation of 3-Selenylindoles
Scheme 3
Scheme 3. Trifluoromethylselenylation of 4- and 7-Azaindoles
Scheme 4
Scheme 4. Metal-Free, Blue-Light Driven Arylation of 4-Anilinocoumarins
Scheme 5
Scheme 5. Selenylation via an EDA Complex
Scheme 6
Scheme 6. Visible-Light Photoredox Catalyzed Trifluoromehylselenation of Aryldiazonium Salts
Scheme 7
Scheme 7. Photocatalyst-Free Preparation of Arylselenides via Arylazo Sulfones
Scheme 8
Scheme 8. Three-Component Preparation of 2-Selanylbenzothiazoles
Scheme 9
Scheme 9. Photoinduced Preparation of (a) 2,3-Bis(selanyl)Quinoxalines and (b) 2,4-Bis-chalcogenated Quinolines
Scheme 10
Scheme 10. Photochemical Route to Selenaheterocycles
Scheme 11
Scheme 11. Synthesis of (a) 1,2- Bis-organylselanyl Alkenes and (b) β-Sulfonylvinylselanes
Scheme 12
Scheme 12. Different Approaches for the Forging of a Vinyl–Se Bond for the Synthesis of (a) 5-Hydroxy-3-selenyl-4a,8a-dihydro-2H-chromen-6(5H)-ones, (b) 3-Selenospiroindolenine, (c) 3-Selanyl-4H-chromen-4-ones
Scheme 13
Scheme 13. Photosensitized Conversion of 1-(1-Arylvinyl)cyclobutanols into β-Selenylated Cyclic Ketones
Scheme 14
Scheme 14. Sunlight Photocatalyzed Preparation of Isoindolinones
Scheme 15
Scheme 15. Functionalization of (a) Styrenes, (b) 2-Vinyl Naphthalenes, and (c) Simple Alkenes
Scheme 16
Scheme 16. Fluoroalkylselenolation of (a) Alkyl Silanes and (b) Alkyl Trifluoroborates
Scheme 17
Scheme 17. Synthesis of 1-Selenocyano-2-cyano Bifunctionalized Alkanes via Selenocyanation of Cyclobutanone Oxime Esters
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