Organocatalytic Three-Component 1,2-Cyanoalkylacylation of Alkenes via Radical Relay
Yu Gao, Yusheng Quan, Zhenjiang Li, Luoyu Gao, Zhihao Zhang, Xin Zou, Rui Yan, Yuanyuan Qu, Kai Guo
Abstract
Here, we report an unprecedented regioselective, intermolecular 1,2-cyanoalkylacylation of feedstock alkenes with readily available oxime esters and aldehydes by N-heterocyclic carbene (NHC) organocatalysis. The crux of this success is the exquisite control over the radical relay process by an NHC organocatalyst. This protocol offers a general platform for diversity-oriented synthesis of valuable ketonitriles under mild, transition-metal-free, and redox-neutral conditions and highlights its potential in the late-stage functionalization of pharmaceutical architectures and natural products.
Topics & Concepts
ChemistryOrganocatalysisRegioselectivityIntermolecular forceSurface modificationCombinatorial chemistryOrganic chemistryCarbeneCatalysisComponent (thermodynamics)UmpolungEnantioselective synthesisMoleculeNucleophilePhysicsThermodynamicsPhysical chemistryN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions