Ligand-Enabled Catalytic C-H Arylation of Aliphatic Amines by a Four-Membered-Ring Cyclopalladation Pathway

Abstract

A palladium-catalyzed CH arylation of aliphatic amines with arylboronic esters is described, proceeding through a four-membered-ring cyclopalladation pathway. Crucial to the successful outcome of this reaction is the action of an amino-acid-derived ligand. A range of hindered secondary amines and arylboronic esters are compatible with this process and the products of the arylation can be advanced to complex polycyclic molecules by sequential CH activation reactions.

Keywords: CH activation; amines; amino acids; homogeneous catalysis; palladium.