Palladium-catalyzed synthesis of N-aryl-2-benzylindolines via tandem arylation of 2-allylaniline: control of selectivity through in situ catalyst modification.

A new synthesis of N-aryl-2-benzylindolines from 2-allylanilines and two different aryl bromides is described. This transformation involves two different sequential metal-catalyzed reactions that lead to the formation of two C-N bonds and one C-C bond in a one-pot process. The selective installation of two different aryl groups in these reactions is accomplished by in situ modification of the palladium catalyst prior to addition of the second aryl bromide.