Paulisch TO, Strieth-Kalthoff F, Henkel C, Pitzer L, Guldi DM, Glorius F (2020)
Publication Type: Journal article
Publication year: 2020
Book Volume: 11
Pages Range: 731-736
Journal Issue: 3
DOI: 10.1039/c9sc04846d
Investigations into the selectivity of intermolecular alkyl radical additions to C-O- vs. 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 in situ 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, i.e. an electron transfer, after reversible radical addition, which eventually propagates the radical chain.
APA:
Paulisch, T.O., Strieth-Kalthoff, F., Henkel, C., Pitzer, L., Guldi, D.M., & Glorius, F. (2020). Chain propagation determines the chemo- And regioselectivity of alkyl radical additions to C-O: Vs. C-C double bonds. Chemical Science, 11(3), 731-736. https://doi.org/10.1039/c9sc04846d
MLA:
Paulisch, Tiffany O., et al. "Chain propagation determines the chemo- And regioselectivity of alkyl radical additions to C-O: Vs. C-C double bonds." Chemical Science 11.3 (2020): 731-736.
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