Chain propagation determines the chemo- And regioselectivity of alkyl radical additions to C-O: Vs. C-C double bonds
Paulisch TO, Strieth-Kalthoff F, Henkel C, Pitzer L, Guldi DM, Glorius F (2020)
Publication Type: Journal article
Publication year: 2020
Journal
Book Volume: 11
Pages Range: 731-736
Journal Issue: 3
DOI: 10.1039/c9sc04846d
Abstract
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.
Authors with CRIS profile
Christian Henkel
Lehrstuhl für Physikalische Chemie I
Dirk Michael Guldi
Lehrstuhl für Physikalische Chemie I
Involved external institutions
Germany (DE)How to cite
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.
BibTeX: Download