Iron-Catalyzed Oxyfunctionalization of Aliphatic Amines at Remote Benzylic C–H Sites

摘要

We report the development of an iron-catalyzed method for the selective oxyfunctionalization of C(sp³)–H bonds in aliphatic amine substrates. This transformation is highly selective for benzylic C–H bonds that are remote (i.e., at least 3-carbons) from the amine functional group. High site selectivity is achieved by in situ protonation of the amine with trifluoroacetic acid, which deactivates more traditionally reactive C–H sites that are α-to nitrogen. The scope and synthetic utility of this method are demonstrated via the synthesis and derivatization of a variety of amine-containing biologically active molecules.