The α-tertiary amine motif drives remarkable selectivity for Pd-catalyzed carbonylation of β-methylene C-H bonds.
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Hogg, K., Trowbridge, A., Alvarez-Pérez, A., & Gaunt, M. (2017). The α-tertiary amine motif drives remarkable selectivity for Pd-catalyzed carbonylation of β-methylene C-H bonds.. Chemical science, 8 (12), 8198-8203. https://doi.org/10.1039/c7sc03876c
The selective C–H carbonylation of methylene bonds in the presence of traditionally more reactive methyl C–H and C(sp2)–H bonds in -tertiary amines is reported. The exceptional selectivity is driven by the bulky -tertiary amine motif, which we hypothesise orientates the activating C–H bond proximal to Pd in order to avoid an unfavourable steric clash with a second a-tertiary amine on the Pd centre, promoting preferential cyclopalladation at the methylene position. The reaction tolerates a range of structurally interesting and synthetically versatile functional groups, delivering the corresponding b-lactam products in good to excellent yields.
European Research Council (259711)
Royal Society (wm140104)
External DOI: https://doi.org/10.1039/c7sc03876c
This record's URL: https://www.repository.cam.ac.uk/handle/1810/276421
Attribution 4.0 International
Licence URL: http://creativecommons.org/licenses/by/4.0/
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