Nickel‐Catalyzed C−N Cross‐Coupling of Primary Imines with Subsequent In Situ [2+2] Cycloaddition or Alkylation

Herein we report a novel method for C-N cross coupling of primary imines using an inexpensive air stable nickel catalyst. This procedure allows for a secondary in situ reaction with moisture sensitive reagents. In this study we also report the concomitant results from a secondary [2+2] cycloaddition and alkylation reaction. A diverse range of substrates were explored to highlight the usefulness of these reactions including products from a cycloaddition pathway, Staudinger synthesis, which have potential for use as -lactam antibiotics.