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Issue 12, 2017
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The α-tertiary amine motif drives remarkable selectivity for Pd-catalyzed carbonylation of β-methylene C–H bonds

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Abstract

The selective C–H carbonylation of methylene bonds in the presence of traditionally more reactive methyl C–H and C(sp2)–H bonds in α-tertiary amines is reported. The exceptional selectivity is driven by the bulky α-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 α-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 β-lactam products in good to excellent yields.

Graphical abstract: The α-tertiary amine motif drives remarkable selectivity for Pd-catalyzed carbonylation of β-methylene C–H bonds

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Publication details

The article was received on 04 Sep 2017, accepted on 08 Oct 2017 and first published on 09 Oct 2017


Article type: Edge Article
DOI: 10.1039/C7SC03876C
Citation: Chem. Sci., 2017,8, 8198-8203
  • Open access: Creative Commons BY license
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    The α-tertiary amine motif drives remarkable selectivity for Pd-catalyzed carbonylation of β-methylene C–H bonds

    K. F. Hogg, A. Trowbridge, A. Alvarez-Pérez and M. J. Gaunt, Chem. Sci., 2017, 8, 8198
    DOI: 10.1039/C7SC03876C

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