Regio‐ and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis
Само за регистроване кориснике
2023
Аутори
Jovanović, MilošJovanović, Predrag
Tasić, Gordana
Simić, Milena R.
Maslak, Veselin
Rakić, Srđan
Rodić, Marko
Vlahović, Filip
Petković, Miloš
Savić, Vladimir
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Enallenylamideshave been utilizedforthe synthesisof heterobicycle[4.2.0]octanederiva-tives via Ir/hν promoted[2+2] cycloadditionreaction.The reactionspecificallytargets the distaldoublebond of the allene moiety, and resultsin theexclusiveformationof thetransproduct.Theprocessis conductedat room temperatureand underan inert atmosphere.An extensivestudy on thesubstituentpropensitiesduringthe cycloadditionstep revealedvariableeffects.Electron-withdrawinggroupsconjugatedwith the doublebond participat-ing in the cycloadditioneither hinderedthe processor reducedits yield. Conversely, electron-donatingsubstituentsenhancedthe efficiency, resultinginproductyields rangingfrom 60% to 88%. Our studyalso demonstratedthe influenceof protectinggroupson the reactionpathway.
Кључне речи:
[2+2] cycloaddition / allenes / photo-chemistry / photocatalysis / iridium / DFTИзвор:
Advanced Synthesis and Catalysis, 2023, 365, 15, 2516-2523Издавач:
- John Wiley and Sons Inc
Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200161 (Универзитет у Београду, Фармацеутски факултет) (RS-MESTD-inst-2020-200161)
Институција/група
IHTMTY - JOUR AU - Jovanović, Miloš AU - Jovanović, Predrag AU - Tasić, Gordana AU - Simić, Milena R. AU - Maslak, Veselin AU - Rakić, Srđan AU - Rodić, Marko AU - Vlahović, Filip AU - Petković, Miloš AU - Savić, Vladimir PY - 2023 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/7166 AB - Enallenylamideshave been utilizedforthe synthesisof heterobicycle[4.2.0]octanederiva-tives via Ir/hν promoted[2+2] cycloadditionreaction.The reactionspecificallytargets the distaldoublebond of the allene moiety, and resultsin theexclusiveformationof thetransproduct.Theprocessis conductedat room temperatureand underan inert atmosphere.An extensivestudy on thesubstituentpropensitiesduringthe cycloadditionstep revealedvariableeffects.Electron-withdrawinggroupsconjugatedwith the doublebond participat-ing in the cycloadditioneither hinderedthe processor reducedits yield. Conversely, electron-donatingsubstituentsenhancedthe efficiency, resultinginproductyields rangingfrom 60% to 88%. Our studyalso demonstratedthe influenceof protectinggroupson the reactionpathway. 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 VL - 365 IS - 15 SP - 2516 EP - 2523 DO - 10.1002/adsc.202300301 ER -
@article{ author = "Jovanović, Miloš and Jovanović, Predrag and Tasić, Gordana and Simić, Milena R. and Maslak, Veselin and Rakić, Srđan and Rodić, Marko and Vlahović, Filip and Petković, Miloš and Savić, Vladimir", year = "2023", abstract = "Enallenylamideshave been utilizedforthe synthesisof heterobicycle[4.2.0]octanederiva-tives via Ir/hν promoted[2+2] cycloadditionreaction.The reactionspecificallytargets the distaldoublebond of the allene moiety, and resultsin theexclusiveformationof thetransproduct.Theprocessis conductedat room temperatureand underan inert atmosphere.An extensivestudy on thesubstituentpropensitiesduringthe cycloadditionstep revealedvariableeffects.Electron-withdrawinggroupsconjugatedwith the doublebond participat-ing in the cycloadditioneither hinderedthe processor reducedits yield. Conversely, electron-donatingsubstituentsenhancedthe efficiency, resultinginproductyields rangingfrom 60% to 88%. Our studyalso demonstratedthe influenceof protectinggroupson the reactionpathway.", 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", volume = "365", number = "15", pages = "2516-2523", doi = "10.1002/adsc.202300301" }
Jovanović, M., Jovanović, P., Tasić, G., Simić, M. R., 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., 365(15), 2516-2523. https://doi.org/10.1002/adsc.202300301
Jovanović M, Jovanović P, Tasić G, Simić MR, 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;365(15):2516-2523. doi:10.1002/adsc.202300301 .
Jovanović, Miloš, Jovanović, Predrag, Tasić, Gordana, Simić, Milena R., 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, 365, no. 15 (2023):2516-2523, https://doi.org/10.1002/adsc.202300301 . .