Cross-coupling reactions of alkenyl halides with 4-alkyl-1,4-dihydropyridines as alkylation reagents have been achieved by combination of nickel and photoredox catalysts. Alkenyl halides bearing alkyl and aryl substituents are available. Particularly, in the use of aryl-substituted alkenyl halides, cross-coupling reactions are associated with E to Z isomerization of alkenes. Thus, Z-isomers of the products are obtained as major products. The present strategy provides a novel synthetic method to control the stereochemistry around alkenes.
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