A Convenient One-Pot Synthesis of a Sterically Demanding Aniline from Aryllithium Using Trimethylsilyl Azide, Conversion to -Diketimines and Synthesis of a -Diketiminate Magnesium Hydride Complex.

This work reports the one-pot synthesis of sterically demanding aniline derivatives from aryllithium species utilising trimethylsilyl azide to introduce amine functionalities and conversions to new examples of a common '-chelating ligand system. The reaction of TripLi (Trip = 2,4,6-Pr-CH) with trimethylsilyl azide afforded the silyltriazene TripNN(SiMe) in situ, which readily reacts with methanol under dinitrogen elimination to the aniline TripNH in good yield. The reaction pathways and by-products of the system have been studied.