Electrochemical Silylation of Electron‐Deficient Heterocycles Using <i>N</i>‐Hydroxyphthalimide as HAT Catalyst
Cong Jiang, Yujie Liao, Heng Li, Zhang Sumin, Ping Liu, Peipei Sun
Abstract
Abstract A practical electrochemical Minisci‐type reaction for the synthesis of silylated heterocycles is described. Using N ‐hydroxyphthalimide (NHPI) as the hydrogen atom transfer (HAT) catalyst and trialkylsilanes as the silyl radical sources, a wide range of electron‐deficient heterocycles in‐cluding quinoline, quinoxaline, phthalazine, 3,6‐dichloropyridazine, phenanthridine, 6‐chloroimidazo[1,2‐ b ]pyridazine and coumarin, etc. were easily converted to the corresponding silylated products in 37–83% yields. magnified image
Topics & Concepts
ChemistryPyridazineQuinolineQuinoxalineSilylationCatalysisPhthalazineElectrochemistryElectron transferMedicinal chemistryPhotochemistryHydrogen atomOrganic chemistryCombinatorial chemistryPolymer chemistryPhysical chemistryElectrodeAlkylRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques