Organic Chemistry Portal



Photoredox-Nickel Dual-Catalyzed C-Alkylation of Secondary Nitroalkanes: Access to Sterically Hindered α-Tertiary Amines

Sina Rezazadeh, Maxwell I. Martin, Raphael S. Kim, Glenn P. A. Yap, Joel Rosenthal and Donald A. Watson*

*Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States, Email:

S. Rezazadeh, M. I. Martin, R. S. Kim, G. P. A. Yap, J. Rosenthal, D. A. Watson, J. Am. Chem. Soc., 2023, 145, 4707-4715.

DOI: 10.1021/jacs.2c13174

see article for more reactions


Use of a nickel catalyst in combination with a photoredox catalyst and light leads to much more active alkylation catalysts for the synthesis of tertiary nitroalkanes via alkylation of secondary nitroalkanes using aliphatic iodides. The conditions are scalable as well as air and moisture tolerant. Importantly, reduction of the tertiary nitroalkane products allows rapid access to α-tertiary amines.

see article for more examples

Key Words

nitro compounds, photochemistry

ID: J48-Y2023