Improved conditions for palladium-catalyzed conversion of diverse aryl bromides to primary anilines

ORGN 614

Swapna Bhagwanth, bhagw002@umn.edu, George M. Adjabeng, george.m.adjabeng@gsk.com, and Keith R. Hornberger, keith.r.hornberger@gsk.com. Department of Chemistry, Oncology Center of Excellence for Drug Discovery, GlaxoSmithKline, 5 Moore Drive, Research Triangle Park, NC 27709
We report Pd-catalyzed conditions for converting diverse aryl bromides to the corresponding primary anilines using benzophenone imine or tert-butyl carbamate as ammonia equivalents. The reaction conditions are mild (RT to 30 °C) and have general substrate scope. In some cases, the methods are complementary with respect to functional group compatibility. In addition, tert-butyl carbamate has emerged as a convenient ammonia equivalent, providing a robust handle (as the Boc-protected aniline) to conduct further reactions prior to deprotection of the aniline.