Palladium-Catalyzed Branch- and Z-Selective Allylic C-H Amination with Aromatic Amines

Abstract

Allylamines are important building blocks in the synthesis of bioactive compounds. The direct coupling of allylic C-H bonds and commonly available amines is a major synthetic challenge. An allylic C-H amination of 1,4-dienes has been accomplished by palladium catalysis. With aromatic amines, branch-selective allylic aminations are favored to generate thermodynamically unstable Z-allylamines. In addition, more basic aliphatic cyclic amines can also engage in the reaction, but linear dienyl allylic amines are the major products.

Keywords: Alkene; Amination; C−H Activation; Palladium Catalysis; Regioselection.