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DOI: 10.1055/s-0042-1751360
Organo-photocatalytic Synthesis of Functionalized Pyrroles from 2H-Azirines and α-Substituted Nitroalkenes
The authors thank the Department of Science & Technology – Science & Engineering Research Board (DST-SERB; project ref. No.: CRG/2020/000752) for financial support. L.D. thanks CSIR, New Delhi, and P.M. thanks UGC, New Delhi, for a Ph.D. Fellowship. A.P. thanks DST-SERB, New Delhi, for a Project Fellowship.
Abstract
An efficient organo-photocatalytic method for the synthesis of tetrasubstituted pyrroles bearing a ketone, ester, alcohol, or nitro group at the 3-position has been developed. The reaction involves visible-light-mediated formal [3+2] dipolar cycloaddition between 2H-azirines and α-substituted nitroalkenes followed by a denitration or debromination sequence. The notable features of the protocol are excellent regioselectivity, wide substrate scope, and high yields of the products.
Key words
2H-azirines - α-substituted nitroalkenes - organophotocatalysis - dipolar cycloaddition - functionalized pyrrolesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751360. Included are copies of the 1H NMR, 13C NMR, and 19F NMR spectra of the products.
- Supporting Information
Publication History
Received: 15 July 2022
Accepted after revision: 05 August 2022
Article published online:
23 August 2022
© 2022. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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