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

A mild and efficient coupling method concerning the reactions of gem-bromonitroalkanes with alpha,alpha-diaryl allyl alcohol trimethylsilyl ethers was reported. A cascade consisting of visible light-induced generation of an alpha-nitroalkyl radical and a subsequent neophyl-type rearrangement was key to realize the coupling reactions. Structurally diverse alpha-aryl-gamma-nitro ketones, especially those bearing a nitrocyclobutyl structure, were prepared in moderate to high yields, which could be converted into spirocyclic nitrones and imines.

Automated summary

A mild and efficient coupling method for the reactions of gem-bromonitroalkanes with alpha,alpha-diaryl allyl alcohol trimethylsilyl ethers was reported. The coupling reactions were realized through a cascade involving visible light-induced generation of an alpha-nitroalkyl radical and a subsequent neophyl-type rearrangement. Structurally diverse alpha-aryl-gamma-nitro ketones, especially those bearing a nitrocyclobutyl structure, were prepared in moderate to high yields, which could be converted into spirocyclic nitrones and imines.