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Issue 22, 2020
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The Fe(iii)-catalyzed decarboxylative cycloaddition of β-ketoacids and 2H-azirines for the synthesis of pyrrole derivatives

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Abstract

An Fe(III)-catalyzed Mannich/decarboxylative ring-expansion reaction for the synthesis of pyrrole derivatives is reported. β-Ketoacids were employed as enolate equivalents of a simple ketone and were coupled with 2H-azirine in a formal [3 + 2] cycloaddition reaction. A series of di-, tri-alkyl/aryl-substituted and fused pyrrole derivatives was obtained in moderate to excellent yields (17–92%) under mild reaction conditions. The products could be synthesized on gram-scale with 5 mol% catalyst loading.

Graphical abstract: The Fe(iii)-catalyzed decarboxylative cycloaddition of β-ketoacids and 2H-azirines for the synthesis of pyrrole derivatives

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Article information


Submitted
10 Aug 2020
Accepted
26 Sep 2020
First published
28 Sep 2020

Org. Chem. Front., 2020,7, 3686-3691
Article type
Research Article

The Fe(III)-catalyzed decarboxylative cycloaddition of β-ketoacids and 2H-azirines for the synthesis of pyrrole derivatives

H. Hu, C. Wang, H. Lai, S. Wang, H. Ni, W. Yu and P. Cao, Org. Chem. Front., 2020, 7, 3686
DOI: 10.1039/D0QO00951B

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