Nickel-Catalyzed Reductive Cleavage of Carbon–Oxygen Bonds in Anisole Derivatives Using Diisopropylaminoborane

Abstract

The catalytic removal of a methoxy group on an aromatic ring allows this group to be used as a traceless activating and directing group for aromatic functionalization reactions. Although several catalytic methods for the reductive cleavage of anisole derivatives have been reported, all are applicable only to π-extended aryl ethers, such as naphthyl and biphenyl ethers, while monocyclic aryl ethers cannot be reduced. Herein, we report a nickel-catalyzed reductive cleavage reaction of C–O bonds in aryl ethers using diisopropylaminoborane as the reducing agent. Unlike previously reported methods, this reducing reagent allows effective C–O bond reduction in a much wider range of aryl ether substrates, including monocyclic and heterocyclic ethers bearing various functional groups.