Selective Reductive Elimination at Alkyl Palladium(IV) by Dissociative Ligand Ionization: Catalytic C(sp3 )-H Amination to Azetidines.
Accepted version
Peer-reviewed
Repository URI
Repository DOI
Change log
Authors
Nappi, Manuel
He, Chuan
Whitehurst, William G
Chappell, Ben GN
Gaunt, Matthew J https://orcid.org/0000-0002-7214-608X
Abstract
A palladium(II)-catalyzed γ-C-H amination of cyclic alkyl amines to deliver highly substituted azetidines is reported. The use of a benziodoxole tosylate oxidant in combination with AgOAc was found to be crucial for controlling a selective reductive elimination pathway to the azetidines. The process is tolerant of a range of functional groups, including structural features derived from chiral α-amino alcohols, and leads to the diastereoselective formation of enantiopure azetidines.
Description
Keywords
C−H activation, azetidines, hypervalent compounds, palladium, reaction mechanisms
Journal Title
Angew Chem Int Ed Engl
Conference Name
Journal ISSN
1433-7851
1521-3773
1521-3773
Volume Title
57
Publisher
Wiley
Publisher DOI
Sponsorship
European Commission Horizon 2020 (H2020) Marie Sk?odowska-Curie actions (702462)
Engineering and Physical Sciences Research Council (EP/N031792/1)
Engineering and Physical Sciences Research Council (1800879)
European Commission (220261)
Engineering and Physical Sciences Research Council (EP/N031792/1)
Engineering and Physical Sciences Research Council (1800879)
European Commission (220261)