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Chain propagation determines the chemo- and regioselectivity of alkyl radical additions to C-O vs. C-C double bonds
Ist Teil von
Chemical science (Cambridge), 2020-01, Vol.11 (3), p.731-736
Ort / Verlag
England: Royal Society of Chemistry
Erscheinungsjahr
2020
Link zum Volltext
Quelle
EZB Free E-Journals
Beschreibungen/Notizen
Investigations into the selectivity of intermolecular alkyl radical additions to C-O-
C-C-double bonds in α,β-unsaturated carbonyl compounds are described. Therefore, a photoredox-initiated radical chain reaction is explored, where the activation of the carbonyl-group through an
generated Lewis acid - originating from the substrate - enables the formation of either C-O or the C-C-addition products. α,β-Unsaturated aldehydes form selectively 1,2-, while esters and ketones form the corresponding 1,4-addition products exclusively. Computational studies lead to reason that this chemo- and regioselectivity is determined by the consecutive step,
an electron transfer, after reversible radical addition, which eventually propagates the radical chain.