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Synthesis of Δ1-Pyrrolines via Formal (3 + 2)-Cycloaddition of 2H-Azirines with Enones Promoted by Visible Light
Lorena S R Martelli1, Lucas G Furniel1, Pedro H O Santiago2
1Centre of Excellence for Research in Sustainable Chemistry, Department of Chemistry, Federal University of São Carlos, São Carlos, São Paulo 13565-905, Brazil.
Abstract:
This work reports the first synthesis of Δ1-pyrrolines promoted by visible light under continuous flow, achieved through the formal (3 + 2)-cycloaddition of 2H-azirines to enones. A total of 22 examples of trisubstituted Δ1-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.
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