Visible-Light-Mediated
Radical Silyl-Oximation of
Activated Alkenes Using tert-Butyl Nitrite and Silanes
Posted on 2022-11-10 - 15:05
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.
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Plöger, Stefanie; Studer, Armido (2022). Visible-Light-Mediated
Radical Silyl-Oximation of
Activated Alkenes Using tert-Butyl Nitrite and Silanes. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.2c03644
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