Visible-Light Photoredox-Catalyzed Formal [5 + 1] Cycloaddition of N‑Tosyl Vinylaziridines with Difluoroalkyl Halides

A visible-light photoredox-catalyzed formal [5 + 1] cycloaddition of N-tosyl vinylaziridines with difluoroalkyl halides as unique C1 synthons was developed. The procedure provides an efficient and practical method to synthesize diverse pyridines in moderate to good yields. The reaction underwent a r...

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Bibliographic Details
Published in:Organic letters 2020-12, Vol.22 (24), p.9658-9664
Main Authors: Liu, Yantao, Luo, Wen, Wang, Zhenjie, Zhao, Yuxin, Zhao, Jingjing, Xu, Xuejun, Wang, Chaojie, Li, Pan
Format: Article
Language:English
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Summary:A visible-light photoredox-catalyzed formal [5 + 1] cycloaddition of N-tosyl vinylaziridines with difluoroalkyl halides as unique C1 synthons was developed. The procedure provides an efficient and practical method to synthesize diverse pyridines in moderate to good yields. The reaction underwent a radical-initiated kinetically controlled ring-opening of vinylaziridines and involved a key α,β-unsaturated imine intermediate, followed by an E2 elimination, a 6π electrocyclization, and defluorinated aromatization.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03718