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Redox-Neutral 1,3-Dipolar Cycloaddition of 2H-Azirines with 2,4,6-Triarylpyrylium Salts under Visible Light Irradiation

Authors :
Ruchir Kant
Namrata Rastogi
Ayushi Pokhriyal
Bhupal Singh Karki
Source :
The Journal of Organic Chemistry. 86:4661-4670
Publication Year :
2021
Publisher :
American Chemical Society (ACS), 2021.

Abstract

A novel visible light mediated redox-neutral 1,3-dipolar cycloaddition of 2H-azirines with 2,4,6-triarylpyrylium tetrafluoroborate salts providing tetrasubstituted pyrroles has been developed. The 2,4,6-triarylpyrylium salt acts as dipolarophile as well as photosensitizer in the reaction, under blue light irradiation. The control experiments indicated single electron oxidation of 2H-azirines by photoexcited pyrylium salts, followed by coupling between an azaallenyl radical cation and triarylpyranyl radical as the key mechanistic feature. The mild conditions, wide substrate scope, and complete regioselectivity are the noticeable attributes of the reaction.

Details

ISSN :
15206904 and 00223263
Volume :
86
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi...........460fa9fcb113404b3c4100ad5f4ac44c
Full Text :
https://doi.org/10.1021/acs.joc.1c00082