Synthesis of Δ<sup>1</sup>-Pyrrolines via Formal (3 + 2)-Cycloaddition of 2<i>H</i>-Azirines with Enones Promoted by Visible Light under Continuous Flow
This work reports the first synthesis of Δ<sup>1</sup>-pyrrolines promoted by visible light under continuous flow, achieved through the formal (3 + 2)-cycloaddition of 2<i>H</i>-azirines to enones. A total of 22 examples of trisubstituted Δ<sup>1</sup>-pyrrolines were prepared in only 30 min of residence time, with 41-93% yield and diastereomeric ratios up to 7:3. Furthermore, continuous flow conditions were also effective when chalcones were used as starting materials, leading to the formation of 7 tetrasubstituted pyrroles with an overall yield ranging from 12 to 47%, via a photocatalyzed cycloaddition-oxidation sequence.
Authors
- Arlene G. Corrêa (ORCID: https://orcid.org/0000-0003-4247-2228)
- Lorena S. R. Martelli (ORCID: https://orcid.org/0000-0001-5939-8672)
- Lucas G. Furniel (ORCID: https://orcid.org/0000-0003-1280-1449)
- Pedro H. O. Santiago (ORCID: https://orcid.org/0000-0001-7841-8480)
- Javier Ellena (ORCID: https://orcid.org/0000-0002-0676-3098)
Institutions
- Universidade Federal de São Carlos (BR)
- Centre for Sustainable Energy (GB)
- FZU ‒ Institute of Physics of the Academy of Sciences of the Czech Republic (CZ)
Publication Details
- Journal
- ACS Omega
- Published
- 2025-04-23
- DOI
- https://doi.org/10.1021/acsomega.5c01416
- Citations
- 3
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 2.81
Funders
- GlaxoSmithKline
- Fundação de Amparo à Pesquisa do Estado de São Paulo
- Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
- Conselho Nacional de Desenvolvimento Científico e Tecnológico