Photoredox‐ and Nickel‐Catalyzed Hydroalkylation of Alkynes with 4‐Alkyl‐1,4‐dihydropyridines: Ligand‐Controlled Regioselectivity
Yulin Zhang, Yoshiaki Tanabe, Shogo Kuriyama, Yoshiaki Nishibayashi
Abstract
Abstract Dual photoredox‐ and nickel‐catalyzed hydroalkylation of terminal alkynes with 4‐alkyl‐1,4‐dihydropyridines under visible light irradiation to afford Markovnikov‐ or anti ‐Markovnikov‐type alkylated alkenes in good‐to‐high yields has been achieved, in which the regioselectivity of the products was effectively controlled by coordination ligands for nickel species. Using [NiCl 2 (dtbbpy)] as a catalyst led to the formation of Markovnikov‐type products, whereas using NiCl 2 ⋅ 6 H 2 O led to the formation of anti ‐Markovnikov‐type products.
Topics & Concepts
Markovnikov's ruleRegioselectivityChemistryAlkylCatalysisAlkylationNickelLigand (biochemistry)Combinatorial chemistryOrganic chemistryMedicinal chemistryBiochemistryReceptorRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques