Zinc Trimethylsilylamide as a Mild Ammonia Equivalent and Base for the Amination of Aryl Halides and Triflates

Zinc Trimethylsilylamide as a Mild Ammonia Equivalent and Base for the Amination of Aryl Halides and Triflates

Org. Lett.  2005,  7,  1169-1172.

We report that Zn[N(SiMe3)2]2 is a mild ammonia equivalent and base for the palladium-catalyzed amination of aryl halides and triflates. In contrast to LiN(SiMe3)2, the combination of Zn[N(SiMe3)2]2 and LiCl coupled with aryl halides and triflates containing base-sensitive functionality in high yields. In addition, aryl bromides coupled with aryl and alkylamines with the combination of Zn[N(SiMe3)2]2 and LiCl as base. These aminations occurred without racemization of the enolizable stereocenter of an optically active ester. Read more on publisher's site.