American Chemical Society
ol2c03644_si_001.pdf (5.43 MB)

Visible-Light-Mediated Radical Silyl-Oximation of Activated Alkenes Using tert-Butyl Nitrite and Silanes

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journal contribution
posted on 2022-11-10, 15:05 authored by Stefanie Plöger, Armido Studer
A metal-free radical 1,2-difunctionalization of activated alkenes with various silanes and tert-butyl nitrite is reported. The radical cascade occurs by light-promoted homolytic O–NO bond cleavage of tert-butyl nitrite and subsequent hydrogen atom abstraction by the alkoxyl radical from the silane. Silyl radical addition to the alkene and highly selective cross-coupling of the NO radical with the Si-adduct C-radical provide the silyl-oximation product in moderate to good yields. The reaction features good functional group tolerance and is easily scaled up.