Metal-catalyzed silylene transfer to imines: Silaaziridine formation and reactivity

ORGN 367

Zulimar Nevárez, znevarez@uci.edu and K. A. Woerpel, kwoerpel@uci.edu. Department of Chemistry, University of California, Irvine, Irvine, CA 92697-0225
The recent developments of metal-catalyzed silylene transfer reactions to imines are presented. Synthetically useful silaaziridines are obtained from the transfer reactions. The scope and limitations of silaaziridine formation are introduced. A systematic study of the reactivity of silaaziridines is also presented which revealed a variety of insertion reactions depending on the reaction conditions employed and the substitution pattern of the silaaziridines. Among these, unexpected dearomatization-cyclization reactions and palladium catalyzed alkyne insertion reactions are shown as well as the development of synthetically useful transformations.