Accessing reactive ketyl-type radicals in mild and controllable ways represents an ambitious target. A study now reports a multicomponent palladium-photocatalysed reaction between aldehydes, 1,3-butadiene and various nucleophiles that affords complex homoallylic alcohols through ketyl-type radicals.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 12 digital issues and online access to articles
$119.00 per year
only $9.92 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
References
Péter, Á., Agasti, S., Knowles, O., Pye, E. & Procter, D. Recent advances in the chemistry of ketyl radicals. Chem. Soc. Rev. 50, 5349–5365 (2021). A review article that compares classical and more modern — for instance, photoredox —approaches to ketyl radicals.
Chuentragool, P., Kurandina, D. & Gevorgyan, V. Catalysis with palladium complexes photoexcited by visible light. Angew. Chem. Int. Ed. 58, 11586–11598 (2019). A review article offering an overview of visible-light-induced palladium photocatalysis.
Huang, H.-M. et al. Catalytic radical generation of π-allylpalladium complexes. Nat. Catal. 3, 393–400 (2020). This paper reports the combination of palladium photogenerated radicals with the Tsuji–Trost reaction.
Ulich, L. H. & Adams, R. The reaction between acid halides and aldehydes. III. J. Am. Chem. Soc. 43, 660–667 (1921). Seminal report of α-oxy bromide generation from aldehydes and acyl bromides.
Wang, L., Lear, J. M., Rafferty, S. M., Fosu, S. C. & Nagib, D. A. Ketyl radical reactivity via atom transfer catalysis. Science 362, 225–229 (2018). This paper reports the generation of ketyl-type radicals from α-oxy iodides under atom transfer catalysis.
Additional information
Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
This is a summary of: Huang, H.-M. et al. Catalytic multicomponent reaction involving a ketyl-type radical. Nat. Synth. https://doi.org/10.1038/s44160-022-00085-6 (2022).
Rights and permissions
About this article
Cite this article
Harnessing ketyl-type radicals using palladium photocatalysis. Nat. Synth 1, 424–425 (2022). https://doi.org/10.1038/s44160-022-00086-5
Published:
Issue Date:
DOI: https://doi.org/10.1038/s44160-022-00086-5
