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

Darren Willcox, Ben G.N. Chappell, Kirsten F. Hogg, Jonas Calleja, Adam P. Smalley, Matthew J. Gaunt

Research output: Contribution to journalArticlepeer-review

Abstract

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.
Original languageEnglish
Pages (from-to)851-857
Number of pages7
JournalScience
Volume354
Issue number6314
DOIs
Publication statusPublished - 18 Nov 2016

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