Visible-Light Photoredox-Catalyzed Formal [5 + 1] Cycloaddition of N‑Tosyl Vinylaziridines with Difluoroalkyl Halides
journal contributionposted on 25.11.2020, 17:08 by Yantao Liu, Wen Luo, Zhenjie Wang, Yuxin Zhao, Jingjing Zhao, Xuejun Xu, Chaojie Wang, Pan Li
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.
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tosyl vinylaziridinesDifluoroalkyl Halidesdefluorinated aromatizationTosylcycloaddition6π electrocyclizationimineC 1 synthonsPhotoredox-CatalyzedmethodFormalring-openingVinylaziridinedifluoroalkyl halidespyridineradical-initiated kineticallyvisible-light photoredox-catalyzedyieldVisible-LightE 2 eliminationCycloadditionprocedure