Iron-Catalyzed Radical Cycloaddition of 2H‑Azirines and Enamides for the Synthesis of Pyrroles

Iron-Catalyzed Radical Cycloaddition of 2H‑Azirines and Enamides for the Synthesis of Pyrroles

A novel and efficient Fe-catalyzed radical cycloaddition of 2H-azirines and enamides for the synthesis of substituted pyrroles has been developed. The radical cycloaddition reaction proceeded through a conceptually new Fe­(II)-catalyzed homolytic cleavage of C–N bond of 2H-azirines sequential radica...

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Bibliographic Details
Published in:Organic letters Vol. 20; no. 5; pp. 1287 - 1290
Main Authors: Zhao, Mi-Na, Ren, Zhi-Hui, Yang, De-Suo, Guan, Zheng-Hui
Format: Journal Article
Language:English
Published: United States American Chemical Society 02-03-2018
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Summary:A novel and efficient Fe-catalyzed radical cycloaddition of 2H-azirines and enamides for the synthesis of substituted pyrroles has been developed. The radical cycloaddition reaction proceeded through a conceptually new Fe­(II)-catalyzed homolytic cleavage of C–N bond of 2H-azirines sequential radical cyclization with enamides. The reaction used readily available starting materials, tolerated various functional groups, and afforded valuable triaryl-substituted pyrroles in good to high yields under mild reaction conditions.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b04007