Efficient Synthesis of 3H-Indoles Enabled by the Lead-Mediated α-Arylation of β-Ketoesters or γ-Lactams Using Aryl Azides

The development of a lead-mediated alpha-arylation reaction between aryl azides and beta-ketoesters or gamma-lactams that facilitates the formation of 3H-indoles is disclosed. Twenty-five examples are included which demonstrate the generality of this reaction to access aryl azides bearing tetrasubstituted o-alkyl substituents. When paired with a Staudinger reduction, this reaction streamlines the synthesis of functionalized 3H-indoles.