Copper(I) Iodide Catalyzed Formation of Aryl Hydrazides from a Mitsunobo Reagent and Aryl Halides

The Mitsonubo reagent (triphenylphosphine and dialkyl azodicarboxylates) was employed as a potential anionic nucleophile in a reaction involving aryl halides to produce aryl hydrazides. Aryl iodides and bromides, with electron-withdrawing as well as electron-releasing groups on the aromatic ring, undergo coupling reactions in good yields. The optimized conditions are developed for aryl iodides at room temperature and for aryl bromides at 60-75 degrees C.