The α-tertiary amine motif drives remarkable selectivity for Pd-catalyzed carbonylation of β-methylene C-H bonds.
Published version
Peer-reviewed
Repository URI
Repository DOI
Change log
Authors
Hogg, Kirsten F https://orcid.org/0000-0002-8292-4412
Trowbridge, Aaron https://orcid.org/0000-0002-5503-8503
Alvarez-Pérez, Andrea https://orcid.org/0000-0002-3785-3096
Gaunt, Matthew J https://orcid.org/0000-0002-7214-608X
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.
Description
Keywords
3402 Inorganic Chemistry, 3405 Organic Chemistry, 34 Chemical Sciences
Journal Title
Chem Sci
Conference Name
Journal ISSN
2041-6520
2041-6539
2041-6539
Volume Title
8
Publisher
Royal Society of Chemistry (RSC)
Publisher DOI
Sponsorship
Engineering and Physical Sciences Research Council (EP/I00548X/1)
The Royal Society (wm140104)
Engineering and Physical Sciences Research Council (EP/N031792/1)
European Research Council (259711)
The Royal Society (wm140104)
Engineering and Physical Sciences Research Council (EP/N031792/1)
European Research Council (259711)