4.8 Article

Iron(II)-Catalyzed Nitrene Transfer Reaction of Sulfoxides with N-Acyloxyamides

Journal

ORGANIC LETTERS
Volume 24, Issue 31, Pages 5674-5678

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c019905674

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Funding

  1. NSFC [21801191, 21572163, 21873074]
  2. Wenzhou Science & Technology Bureau [2021G0027, G20210032]

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An iron(II)-catalyzed nitrene transfer reaction of sulfoxides with N-acyloxyamides has been developed, leading to the efficient construction of N-acyl sulfoximines with high functional-group compatibility. The methodology can be carried out under an air atmosphere at ambient temperature and can be scaled up to gram scale with a catalyst loading of 1 mol %. The application of the methodology was demonstrated by facile C-H acetoxylation and olefination using the N-acyl sulfoximine as the directing group.
An iron(II)-catalyzed nitrene transfer reaction of sulfoxides with N-acyloxyamides has been developed, leading to the efficient construction of N-acyl sulfoximines with high functional-group compatibility. The current catalytic transformation was carried out under an air atmosphere at ambient temperature and could be scaled up to gram scale with a catalyst loading of 1 mol %. Application of the methodology was demonstrated by facile C-H acetoxylation and olefination using the N-acyl sulfoximine as the directing group.

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