Nickel-Catalyzed Reductive Alkylation of Aldimines with Unactivated Alkyl Iodides

The reaction proceeds at ambient temperature and accommodates unactivated primary, secondary, and tertiary alkyl iodides as well as selected activated alkyl bromides with broad functional-group tolerance. Complex molecule-derived alkyl iodides, a gram-scale reaction, and β-amino ester derivatizations demonstrate synthetic utility.

Mechanistic studies support nickel-mediated generation of a solution-accessible alkyl radical and are consistent with outer-sphere radical addition to the imine.