Dual Role of the Arylating Agent in a Highly C(2)-Selective Pd-Catalysed Functionalisation of Pyrrole Derivatives
Само за регистроване кориснике
2022
Аутори
Petković, Miloš![](/themes/MirageFarFaR/images/orcid.png)
Jovanović, Miloš
![](/themes/MirageFarFaR/images/orcid.png)
Jovanović, Predrag
![](/themes/MirageFarFaR/images/orcid.png)
Simić, Milena
![](/themes/MirageFarFaR/images/orcid.png)
Tasić, Gordana
![](/themes/MirageFarFaR/images/orcid.png)
Savić, Vladimir
![](/themes/MirageFarFaR/images/orcid.png)
Чланак у часопису (Објављена верзија)
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Метаподаци
Приказ свих података о документуАпстракт
Pyrrole derivatives with C(2)-aryl substituents are an important and widespread class of heterocyclic compounds. Their synthesis can be accomplished using several strategic variants which usually entail either protection of the N–H functionality followed by the arylation, or a direct arylation. Although direct arylation is a preferable process due to a reduced number of synthetic steps, it often requires vigorous conditions or challenging reagents. To this synthetic repertoire, we add a novel method that is based on the dual role of the arylating agent. It serves as the nitrogen protecting group while also being involved in the arylation step. Deprotection as a final stage is carried out simultaneously utilising amines as reacting components. This approach ensures relatively mild conditions and exclusive C(2) selectivity yielding 2-arylpyrroles with the amide functionality. While aromatic amines are not suitable partners under studied conditions, most likely due to lower nucleophilicit...y, aliphatic amines, either primary or secondary, afford products in good yields.
Кључне речи:
pyrroles / palladium / catalysis / arylation / regioselectivityИзвор:
Synthesis, 2022, 54, 12, 2839-2848Издавач:
- Georg Thieme Verlag
Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200161 (Универзитет у Београду, Фармацеутски факултет) (RS-MESTD-inst-2020-200161)
DOI: 10.1055/a-1758-6312
ISSN: 0039-7881
WoS: 000802351400010
Scopus: 2-s2.0-85128209812
Институција/група
PharmacyTY - JOUR AU - Petković, Miloš AU - Jovanović, Miloš AU - Jovanović, Predrag AU - Simić, Milena AU - Tasić, Gordana AU - Savić, Vladimir PY - 2022 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4720 AB - Pyrrole derivatives with C(2)-aryl substituents are an important and widespread class of heterocyclic compounds. Their synthesis can be accomplished using several strategic variants which usually entail either protection of the N–H functionality followed by the arylation, or a direct arylation. Although direct arylation is a preferable process due to a reduced number of synthetic steps, it often requires vigorous conditions or challenging reagents. To this synthetic repertoire, we add a novel method that is based on the dual role of the arylating agent. It serves as the nitrogen protecting group while also being involved in the arylation step. Deprotection as a final stage is carried out simultaneously utilising amines as reacting components. This approach ensures relatively mild conditions and exclusive C(2) selectivity yielding 2-arylpyrroles with the amide functionality. While aromatic amines are not suitable partners under studied conditions, most likely due to lower nucleophilicity, aliphatic amines, either primary or secondary, afford products in good yields. PB - Georg Thieme Verlag T2 - Synthesis T1 - Dual Role of the Arylating Agent in a Highly C(2)-Selective Pd-Catalysed Functionalisation of Pyrrole Derivatives VL - 54 IS - 12 SP - 2839 EP - 2848 DO - 10.1055/a-1758-6312 ER -
@article{ author = "Petković, Miloš and Jovanović, Miloš and Jovanović, Predrag and Simić, Milena and Tasić, Gordana and Savić, Vladimir", year = "2022", abstract = "Pyrrole derivatives with C(2)-aryl substituents are an important and widespread class of heterocyclic compounds. Their synthesis can be accomplished using several strategic variants which usually entail either protection of the N–H functionality followed by the arylation, or a direct arylation. Although direct arylation is a preferable process due to a reduced number of synthetic steps, it often requires vigorous conditions or challenging reagents. To this synthetic repertoire, we add a novel method that is based on the dual role of the arylating agent. It serves as the nitrogen protecting group while also being involved in the arylation step. Deprotection as a final stage is carried out simultaneously utilising amines as reacting components. This approach ensures relatively mild conditions and exclusive C(2) selectivity yielding 2-arylpyrroles with the amide functionality. While aromatic amines are not suitable partners under studied conditions, most likely due to lower nucleophilicity, aliphatic amines, either primary or secondary, afford products in good yields.", publisher = "Georg Thieme Verlag", journal = "Synthesis", title = "Dual Role of the Arylating Agent in a Highly C(2)-Selective Pd-Catalysed Functionalisation of Pyrrole Derivatives", volume = "54", number = "12", pages = "2839-2848", doi = "10.1055/a-1758-6312" }
Petković, M., Jovanović, M., Jovanović, P., Simić, M., Tasić, G.,& Savić, V.. (2022). Dual Role of the Arylating Agent in a Highly C(2)-Selective Pd-Catalysed Functionalisation of Pyrrole Derivatives. in Synthesis Georg Thieme Verlag., 54(12), 2839-2848. https://doi.org/10.1055/a-1758-6312
Petković M, Jovanović M, Jovanović P, Simić M, Tasić G, Savić V. Dual Role of the Arylating Agent in a Highly C(2)-Selective Pd-Catalysed Functionalisation of Pyrrole Derivatives. in Synthesis. 2022;54(12):2839-2848. doi:10.1055/a-1758-6312 .
Petković, Miloš, Jovanović, Miloš, Jovanović, Predrag, Simić, Milena, Tasić, Gordana, Savić, Vladimir, "Dual Role of the Arylating Agent in a Highly C(2)-Selective Pd-Catalysed Functionalisation of Pyrrole Derivatives" in Synthesis, 54, no. 12 (2022):2839-2848, https://doi.org/10.1055/a-1758-6312 . .