N-Heterocyclic Carbene/Magnesium Cocatalyzed Radical Relay Assembly of Aliphatic Keto Nitriles
Lei Chen, Shiyi Jin, Jian Gao, Tongtong Liu, Yuebo Shao, Jie Feng, Kangyi Wang, Tao Lu, Ding Du
Abstract
An unprecedented N-heterocyclic carbene and magnesium cocatalyzed three-component acylcyanoalkylation of alkenes with cycloketone oxime esters and aldehydes is presented. This method displayed good scope generality, providing a transition-metal- and photoredox-free pathway to access various multifunctionalized aliphatic keto nitrile structures under mild reaction conditions. Moreover, this strategy is supposed to follow a radical relay mechanism via a single electron transfer event of a Mg/matched Breslow intermediate/oxime ester electron-donating acceptor (EDA) complex.
Topics & Concepts
ChemistryMagnesiumCarbeneNitrileOximeCombinatorial chemistryElectron transferPhotochemistryAcceptorMedicinal chemistryOrganic chemistryCatalysisCondensed matter physicsPhysicsN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions