Photoinduced Copper-Catalyzed Radical Aminocarbonylation of Cycloketone Oxime Esters

A visible light-induced and exogenous photosensitizer-free, copper-catalyzed radical aminocarbonylation of cycloketone oxime esters with CO gas and amines is developed. The mild catalytic system involving CuCl and N,N,N-tridentate ligand shows good reactivity and chemoselectivity, and tolerates a wi...

Full description

Saved in:
Bibliographic Details
Published inACS catalysis Vol. 9; no. 9; pp. 8159 - 8164
Main Authors Lu, Bin, Cheng, Ying, Chen, Li-Yan, Chen, Jia-Rong, Xiao, Wen-Jing
Format Journal Article
LanguageEnglish
Published American Chemical Society 06.09.2019
Subjects
copper catalysis
amides
nitriles
radical carbonylation
photochemistry
oxime esters
aminocarbonylation
Online AccessGet full text

Cover

More Information
Summary:A visible light-induced and exogenous photosensitizer-free, copper-catalyzed radical aminocarbonylation of cycloketone oxime esters with CO gas and amines is developed. The mild catalytic system involving CuCl and N,N,N-tridentate ligand shows good reactivity and chemoselectivity, and tolerates a wide range of cycloketone oxime esters and alkyl/aryl amines, giving the corresponding cyanoalkylated amides in moderate to good yields. Preliminary mechanistic studies suggest that the reaction involves a CuI/CuII/CuIII-based catalytic cycle and radical intermediate.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.9b02830