Design of a Photoredox Catalyst that Enables the Direct Synthesis of Carbamate-Protected Primary Amines via Photoinduced, Copper-Catalyzed N-Alkylation Reactions of Unactivated Secondary Halides
Jun Myun Ahn, Jonas C. Peters* and Gregory C. Fu*
*Division of Chemistry and Chemical Engineering, California
Institute of Technology, Pasadena, California 91125, United States, Email:
gcfu
caltech.edu, jpeterscaltech.edu
J. M. Ahn, J. C. Peters, G. C. Fu, J. Am. Chem. Soc., 2017, 139, 18101-18106.
DOI: 10.1021/jacs.7b10907
see article for more reactions
Abstract
A copper-based photoredox catalyst, bearing a tridentate carbazolide/bisphosphine ligand, that can be activated upon irradiation by blue LEDs, achieves the coupling of a range of primary carbamates with unactivated secondary alkyl bromides at room temperature.
see article for more examples
proposed mechanism
Copper-Catalyzed Alkylation of Aliphatic Amines Induced by Visible Light
C. D. Matier, J. Schwaben, J. C. Peteres, G. C. Fu, J. Am. Chem. Soc., 2017, 139, 17707-17710.
Key Words
protected primary amines, carbamates, tert-butyl carbamates
ID: J48-Y2017
