Iron-Catalyzed Ortho-Allylation of Aromatic Carboxamides with Allyl Ethers

Arenes possessing an N-(quinolin-8-yl)-amide directing group are ortho-allylated with allyl phenyl ether in the presence of an iron/diphosphine catalyst and an organometallic base at 50-70 degrees C. The reaction proceeds via fast iron-catalyzed C-H activation, followed by reaction of the resulting iron intermediate with the allyl ether in gamma-selective fashion.