Synthesis of γ-Oxo-phosphonates via <i>N</i>-Heterocyclic Carbene-Catalyzed Acylphosphorylation of Alkenes
Jia‐Nan Mo, Shengbin Sun, Huiwei Xu, Hanyu Shu, Jiannan Zhao
Abstract
-heterocyclic carbene-catalyzed method for the radical acylphosphorylation of alkenes. Electrochemical investigations were employed to identify an appropriate class of oxime phosphonates capable of undergoing a single-electron transfer (SET) with Breslow enolates. The resulting phosphoryl radicals were effectively coupled with diverse styrenes and aldehydes to yield a variety of γ-oxo-phosphonates. Both radical clock experiments and electrochemical studies support our reaction design, and a plausible mechanism for the organocatalytic transformation is proposed.
Topics & Concepts
ChemistryCarbeneYield (engineering)CatalysisCombinatorial chemistryRadicalElectrochemistryElectron transferOrganic chemistryElectrodeMaterials scienceMetallurgyPhysical chemistryRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesN-Heterocyclic Carbenes in Organic and Inorganic Chemistry