Nickel Catalyzed Regiodivergent Cross-Coupling Alkylation of Aryl Halides with Redox-Active Imines

The advent and development of photoredox/nickel synergistic catalysis have enabled the use of various alkyl radical precursors in the cross-coupling arylation, yet none has addressed the challenge of regiodivergent synthesis. Herein, we disclose a visible light nickel-catalyzed protocol for the deaminative cross-coupling of redox-active imines with various electrophiles that allow for the rapid construction of C(sp(3)) enriched arene architectures in a regiodivergent manner. Key to the success of this protocol is the combination of a readily available organic photocatalyst and a Lewis acid additive. As an additional approach to alkylarenes, we also showcase that the nature of electrophiles dictates the regiochemical outcome.

Automated summary

The advent and development of photoredox/nickel synergistic catalysis have enabled the use of various alkyl radical precursors in the cross-coupling arylation and addressed the challenge of regiodivergent synthesis. We disclose a visible light nickel-catalyzed protocol for the deaminative cross-coupling of redox-active imines with various electrophiles, allowing for the rapid construction of C(sp(3)) enriched arene architectures in a regiodivergent manner.