Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis
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2023
Authors
Jovanović, Miloš
Jovanović, Predrag

Tasić, Gordana

Simić, Milena

Maslak, Veselin

Rakić, Srđan
Rodić, Marko

Vlahović, Filip
Petković, Miloš

Savić, Vladimir

Article (Published version)

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Enallenylamides have been utilized for the synthesis of heterobicycle[4.2.0]octane derivatives via Ir/hν promoted [2+2] cycloaddition reaction. The reaction specifically targets the distal double bond of the allene moiety, and results in the exclusive formation of the trans product. The process is conducted at room temperature and under an inert atmosphere. An extensive study on the substituent propensities during the cycloaddition step revealed variable effects. Electron-withdrawing groups conjugated with the double bond participating in the cycloaddition either hindered the process or reduced its yield. Conversely, electron-donating substituents enhanced the efficiency, resulting in product yields ranging from 60% to 88%. Our study also demonstrated the influence of protecting groups on the reaction pathway.
Keywords:
[2+2] cycloaddition / allenes / DFT / iridium / photocatalysis / photochemistrySource:
Advanced Synthesis and Catalysis, 2023Publisher:
- John Wiley and Sons Inc
Funding / projects:
DOI: 10.1002/adsc.202300301
ISSN: 1615-4150
WoS: 001030558300001
Scopus: 2-s2.0-85164993920
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Institution/Community
PharmacyTY - JOUR AU - Jovanović, Miloš AU - Jovanović, Predrag AU - Tasić, Gordana AU - Simić, Milena AU - Maslak, Veselin AU - Rakić, Srđan AU - Rodić, Marko AU - Vlahović, Filip AU - Petković, Miloš AU - Savić, Vladimir PY - 2023 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4953 AB - Enallenylamides have been utilized for the synthesis of heterobicycle[4.2.0]octane derivatives via Ir/hν promoted [2+2] cycloaddition reaction. The reaction specifically targets the distal double bond of the allene moiety, and results in the exclusive formation of the trans product. The process is conducted at room temperature and under an inert atmosphere. An extensive study on the substituent propensities during the cycloaddition step revealed variable effects. Electron-withdrawing groups conjugated with the double bond participating in the cycloaddition either hindered the process or reduced its yield. Conversely, electron-donating substituents enhanced the efficiency, resulting in product yields ranging from 60% to 88%. Our study also demonstrated the influence of protecting groups on the reaction pathway. PB - John Wiley and Sons Inc T2 - Advanced Synthesis and Catalysis T1 - Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis DO - 10.1002/adsc.202300301 ER -
@article{ author = "Jovanović, Miloš and Jovanović, Predrag and Tasić, Gordana and Simić, Milena and Maslak, Veselin and Rakić, Srđan and Rodić, Marko and Vlahović, Filip and Petković, Miloš and Savić, Vladimir", year = "2023", abstract = "Enallenylamides have been utilized for the synthesis of heterobicycle[4.2.0]octane derivatives via Ir/hν promoted [2+2] cycloaddition reaction. The reaction specifically targets the distal double bond of the allene moiety, and results in the exclusive formation of the trans product. The process is conducted at room temperature and under an inert atmosphere. An extensive study on the substituent propensities during the cycloaddition step revealed variable effects. Electron-withdrawing groups conjugated with the double bond participating in the cycloaddition either hindered the process or reduced its yield. Conversely, electron-donating substituents enhanced the efficiency, resulting in product yields ranging from 60% to 88%. Our study also demonstrated the influence of protecting groups on the reaction pathway.", publisher = "John Wiley and Sons Inc", journal = "Advanced Synthesis and Catalysis", title = "Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis", doi = "10.1002/adsc.202300301" }
Jovanović, M., Jovanović, P., Tasić, G., Simić, M., Maslak, V., Rakić, S., Rodić, M., Vlahović, F., Petković, M.,& Savić, V.. (2023). Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis. in Advanced Synthesis and Catalysis John Wiley and Sons Inc.. https://doi.org/10.1002/adsc.202300301
Jovanović M, Jovanović P, Tasić G, Simić M, Maslak V, Rakić S, Rodić M, Vlahović F, Petković M, Savić V. Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis. in Advanced Synthesis and Catalysis. 2023;. doi:10.1002/adsc.202300301 .
Jovanović, Miloš, Jovanović, Predrag, Tasić, Gordana, Simić, Milena, Maslak, Veselin, Rakić, Srđan, Rodić, Marko, Vlahović, Filip, Petković, Miloš, Savić, Vladimir, "Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis" in Advanced Synthesis and Catalysis (2023), https://doi.org/10.1002/adsc.202300301 . .