Visible-light promoted photoredox catalysis in flow: addition of biologically important α‑amino radicals to michael acceptors
Само за регистроване кориснике
2023
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Visible light promoted photoredox catalyzed formation of α-amino radicals from cyclic tertiary amine compounds and their subsequent addition to Michael acceptors performed in flow conditions allowed access to a wide range of functionalized N-aryl-substituted tetrahydroisoquinolines (THIQs) and N-aryl-substituted tetrahydro-β-carbolines (THBCs). Visible light in conjunction with Ru(bpy)3Cl2 photocatalyst allowed the formation and high reactivities of α-amino radicals in flow conditions at room temperature. These reactions gave valuable products with high efficiencies; some previously unavailable reaction pathways photo or thermal reaction conditions; i.e. direct synthesis of 1-substituted (THBCs) via α-amino radical path were successfully realized in flow. The use of custom-made FEP tube microreactor proved to be the key to succesfull α-amino-radical formation and overall reaction performance in flow. Three types of light transparent custom-made microfluidic devices were tested, among t...hem glass/silicon and FEP type reactor showed very good results in the conversion of tested compounds. Plausible reaction mechanism is proposed in accordance with known principles of photo activation of tertiary amines.
Кључне речи:
Flow chemistry / Microfluidic devices / Photoredox catalysis / Tertahydroisoquinolines / Tetrahydro-β-carbolines / α -amino radicalsИзвор:
Photochemical & Photobiological Sciences, 2023Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200026 (Универзитет у Београду, Институт за хемију, технологију и металургију - ИХТМ) (RS-MESTD-inst-2020-200026)
Институција/група
VinčaTY - JOUR AU - Filipović, Ana AU - Džambaski, Zdravko AU - Bondžić, Aleksandra M. AU - Bondžić, Bojan P. PY - 2023 UR - https://vinar.vin.bg.ac.rs/handle/123456789/11171 AB - Visible light promoted photoredox catalyzed formation of α-amino radicals from cyclic tertiary amine compounds and their subsequent addition to Michael acceptors performed in flow conditions allowed access to a wide range of functionalized N-aryl-substituted tetrahydroisoquinolines (THIQs) and N-aryl-substituted tetrahydro-β-carbolines (THBCs). Visible light in conjunction with Ru(bpy)3Cl2 photocatalyst allowed the formation and high reactivities of α-amino radicals in flow conditions at room temperature. These reactions gave valuable products with high efficiencies; some previously unavailable reaction pathways photo or thermal reaction conditions; i.e. direct synthesis of 1-substituted (THBCs) via α-amino radical path were successfully realized in flow. The use of custom-made FEP tube microreactor proved to be the key to succesfull α-amino-radical formation and overall reaction performance in flow. Three types of light transparent custom-made microfluidic devices were tested, among them glass/silicon and FEP type reactor showed very good results in the conversion of tested compounds. Plausible reaction mechanism is proposed in accordance with known principles of photo activation of tertiary amines. T2 - Photochemical & Photobiological Sciences T1 - Visible-light promoted photoredox catalysis in flow: addition of biologically important α‑amino radicals to michael acceptors DO - 10.1007/s43630-023-00448-8 ER -
@article{ author = "Filipović, Ana and Džambaski, Zdravko and Bondžić, Aleksandra M. and Bondžić, Bojan P.", year = "2023", abstract = "Visible light promoted photoredox catalyzed formation of α-amino radicals from cyclic tertiary amine compounds and their subsequent addition to Michael acceptors performed in flow conditions allowed access to a wide range of functionalized N-aryl-substituted tetrahydroisoquinolines (THIQs) and N-aryl-substituted tetrahydro-β-carbolines (THBCs). Visible light in conjunction with Ru(bpy)3Cl2 photocatalyst allowed the formation and high reactivities of α-amino radicals in flow conditions at room temperature. These reactions gave valuable products with high efficiencies; some previously unavailable reaction pathways photo or thermal reaction conditions; i.e. direct synthesis of 1-substituted (THBCs) via α-amino radical path were successfully realized in flow. The use of custom-made FEP tube microreactor proved to be the key to succesfull α-amino-radical formation and overall reaction performance in flow. Three types of light transparent custom-made microfluidic devices were tested, among them glass/silicon and FEP type reactor showed very good results in the conversion of tested compounds. Plausible reaction mechanism is proposed in accordance with known principles of photo activation of tertiary amines.", journal = "Photochemical & Photobiological Sciences", title = "Visible-light promoted photoredox catalysis in flow: addition of biologically important α‑amino radicals to michael acceptors", doi = "10.1007/s43630-023-00448-8" }
Filipović, A., Džambaski, Z., Bondžić, A. M.,& Bondžić, B. P.. (2023). Visible-light promoted photoredox catalysis in flow: addition of biologically important α‑amino radicals to michael acceptors. in Photochemical & Photobiological Sciences. https://doi.org/10.1007/s43630-023-00448-8
Filipović A, Džambaski Z, Bondžić AM, Bondžić BP. Visible-light promoted photoredox catalysis in flow: addition of biologically important α‑amino radicals to michael acceptors. in Photochemical & Photobiological Sciences. 2023;. doi:10.1007/s43630-023-00448-8 .
Filipović, Ana, Džambaski, Zdravko, Bondžić, Aleksandra M., Bondžić, Bojan P., "Visible-light promoted photoredox catalysis in flow: addition of biologically important α‑amino radicals to michael acceptors" in Photochemical & Photobiological Sciences (2023), https://doi.org/10.1007/s43630-023-00448-8 . .