Nickel-Photoredox-Catalyzed Stereoconvergent Coupling of Alkenyl Halides and Nitrogen-Containing Heterocycles.

Nitrogen-containing heterocycles possessing N -alkenyl substituents are an important structural motif. However, the synthetic methods reported thus far cannot selectively synthesize the Z stereoisomer on the basis of the stereochemistry of the substituted alkenes. Herein, we report the stereoconvergent coupling of heterocycles and alkenyl halides consisting of a mixture of E / Z stereoisomers, which selectively afforded the thermodynamically less stable Z -coupling product. Mechanistic studies suggest that a nickel photoredox catalyst facilitates the formation of N -centered heteroarene radicals.