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gem -Bromonitroalkane Involved Radical 1,2-Aryl Migration of α,α-Diaryl Allyl Alcohol TMS Ether via Visible-Light Photoredox Catalysis.

Shanshan MaYawen GuoLidong LiuLin ShiXingyu LeiXin-Fang DuanPeng Jiao
Published in: The Journal of organic chemistry (2023)
A mild and efficient coupling method concerning the reactions of gem -bromonitroalkanes with α,α-diaryl allyl alcohol trimethylsilyl ethers was reported. A cascade consisting of visible-light-induced generation of an α-nitroalkyl radical and a subsequent neophyl-type rearrangement was key to realize the coupling reactions. Structurally diverse α-aryl-γ-nitro ketones, especially those bearing a nitrocyclobutyl structure, were prepared in moderate to high yields, which could be converted into spirocyclic nitrones and imines.
Keyphrases
  • visible light
  • room temperature
  • alcohol consumption
  • transcranial magnetic stimulation
  • high intensity
  • ionic liquid
  • high frequency