Enantioselective Synthesis of N-alkylated Indoles Enabled by Nickel-Catalyzed C(sp3)-C(sp3) Coupling

Although considerable efforts have been made to construct chiral functionalized indoles, the catalytic and efficient method to access a diverse range of chiral N-alkylated indoles bearing a stereocenter with two minimally different alkyl groups at the N-1 position from readily accessible substrates remains limited. Here, we describe a modular Ni-catalyzed C(sp3)-C(sp3) cross-coupling strategy that couples an array of N-indolyl-substituted alkenes with alkyl iodides to yield chiral α,α-dialkyl indoles in single regioisomeric form, in up to 90% yield and 99% ee.