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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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Supplementary files

Article information


Submitted
04 Sep 2017
Accepted
08 Oct 2017
First published
09 Oct 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 8198-8203
Article type
Edge Article

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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