Photoredox-Nickel Dual-Catalyzed <i>C</i>-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, Donald A. Watson
Abstract
The preparation of tertiary nitroalkanes via the nickel-catalyzed alkylation of secondary nitroalkanes using aliphatic iodides is reported. Previously, catalytic access to this important class of nitroalkanes via alkylation has not been possible due to the inability of catalysts to overcome the steric demands of the products. However, we have now found that the use of a nickel catalyst in combination with a photoredox catalyst and light leads to much more active alkylation catalysts. These can now access tertiary nitroalkanes. 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.