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A general catalytic β-C–H carbonylation of aliphatic amines to β-lactams

Willcox, Darren, Chappell, Ben G. N., Hogg, Kirsten F., Calleja, Jonas, Smalley, Adam P. and Gaunt, Matthew J. 2016. A general catalytic β-C–H carbonylation of aliphatic amines to β-lactams. Science 354 (6314) , pp. 851-857. 10.1126/science.aaf9621

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Methods for the synthesis and functionalization of amines are intrinsically important to a variety of chemical applications. We present a general carbon-hydrogen bond activation process that combines readily available aliphatic amines and the feedstock gas carbon monoxide to form synthetically versatile value-added amide products. The operationally straightforward palladium-catalyzed process exploits a distinct reaction pathway, wherein a sterically hindered carboxylate ligand orchestrates an amine attack on a palladium anhydride to transform aliphatic amines into β-lactams. The reaction is successful with a wide range of secondary amines and can be used as a late-stage functionalization tactic to deliver advanced, highly functionalized amine products of utility for pharmaceutical research and other areas.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: American Association for the Advancement of Science
ISSN: 0036-8075
Date of First Compliant Deposit: 30 May 2019
Date of Acceptance: 18 November 2016
Last Modified: 05 Apr 2020 11:10

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