Synthesis of Polysubstituted Enamides by Hydrogen Atom Transfer Alkene Isomerization Using Dual Cobalt/Photoredox Catalysis
Yusuke Seino, Yuto Yamaguchi, Akihiko Suzuki, Masaaki Yamashita, Yuji Kamei, Futa Kamiyama, Tatsuhiko Yoshino, M. Kojima, Shigeki Matsunaga
Abstract
M-HAT isomerization is a highly reliable method to access thermodynamically stable alkenes with high functional group tolerance. However, synthesis of heteroatom-substituted alkenes by M-HAT isomerization reaction is still underdeveloped. Herein, we report an enamide synthesis using M-HAT via a combination of cobalt and photoredox catalysis. This method tolerates a variety of functional groups including haloarenes, heteroarenes, free hydroxy groups, non-protected indoles, and drug derivatives. Furthermore, this method can isomerize styrene derivatives in good yield and E/Z selectivity.
Topics & Concepts
IsomerizationCobaltChemistryCatalysisAlkeneYield (engineering)HeteroatomAtom economyFunctional groupCombinatorial chemistryHydrogen atomPhotochemistryOrganic chemistryGroup (periodic table)Materials sciencePolymerRing (chemistry)MetallurgyCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsRadical Photochemical Reactions