title: A general catalytic β-C-H carbonylation of aliphatic amines to β-lactams.
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.
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK.
authors.forename: Darren
authors.initials: D
authors.lastname: Willcox
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK.
authors.forename: Ben G N
authors.initials: BG
authors.lastname: Chappell
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK.
authors.forename: Kirsten F
authors.initials: KF
authors.lastname: Hogg
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK.
authors.forename: Jonas
authors.initials: J
authors.lastname: Calleja
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK.
authors.forename: Adam P
authors.initials: AP
authors.lastname: Smalley
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK. mjg32@cam.ac.uk.
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Gaunt
mesh_terms: D000588:Amines / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002248:Carbon Monoxide; D002384:Catalysis; D006860:Hydrogen Bonding; D010165:Palladium / Q000737:chemistry; D047090:beta-Lactams / Q000138:chemical synthesis*
chemical_list: D000588:Amines; D047090:beta-Lactams; D010165:Palladium; D002244:Carbon; D002248:Carbon Monoxide