posted on 2022-11-10, 15:05authored byStefanie 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.