Herein, we report a new method for the C-N cross-coupling of primary imines by using an inexpensive air-stable nickel catalyst. This procedure allows for a subsequent insitu reaction with moisture-sensitive reagents. In this study, we also report secondary [2+2] cycloaddition and alkylation reactions. A diverse range of substrates were explored to highlight the usefulness of this combination of reactions. The reaction products from the cycloaddition pathway, through a Staudinger reaction, have potential applications as β-lactam antibiotics.