We report a photocatalytic Barbier-type allylation of various aldehydes and ketones with allyl bromide for the synthesis of homoallylic alcohols enabled by dual titanium and photoredox catalysis. This environmentally benign...
The
concept of “umpolung” reactivity of π-allylmetal
complexes has been developed as a powerful method for the allylation
of aldehydes. This paper describes the photocatalytic umpolung strategy
for the synthesis of nucleophilic allylcobalt complexes through a
single-electron-transfer (SET) process. This strategy enables the
metallaphotoredox allylation of carbonyls with allyl acetate using
organic N,N-diisopropylethylamine
as the terminal reductant bypassing the use of a stoichiometric amount
of metals. Ultraviolet–visible spectroscopy was used to monitor
the redox changes of cobalt in the reaction.
This work reports the first visible-light mediated cobalt-catalyzed aldehyde allylation with simple alkenes to produce homo-allylic alcohols. This novel strategy directly uses easily available unactivated alkenes as allyl sources instead of pre-synthesized allylic halides.
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