Repository logo
 

Selective Reductive Elimination at Alkyl Palladium(IV) by Dissociative Ligand Ionization: Catalytic C(sp3 )-H Amination to Azetidines.

Accepted version
Peer-reviewed

Loading...
Thumbnail Image

Type

Article

Change log

Authors

Nappi, Manuel 
He, Chuan 
Whitehurst, William G 
Chappell, Ben GN 

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

Volume Title

57

Publisher

Wiley
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)