Cooperative NHC and Photoredox Catalysis for the Synthesis of 1,4-Dicarbonyl Compounds via Diacylation of Alkenes
Shihao Li, Haojun Shu, Sheng Wang, Wenqing Yang, Fei Tang, Xiaoxuan Li, Shilu Fan, Yi‐Si Feng
Abstract
An intermolecular 1,2-diacylation of alkenes is disclosed via cooperative N-heterocyclic carbene and photoredox catalysis under the mediation of PPh3 and Cs2CO3. This protocol provides a practical approach for construction of 1,4-dicarbonyl compounds toward novel diketone and pharmaceutical derivatives. Furthermore, the regioselective dicarbonyl compounds can be synthesized by adding acyl azolium salt. Mechanistic investigations suggest that the process was a critical radical/radical cross coupling of ketyl radicals with benzylic C-radicals.
Topics & Concepts
ChemistryKetylRadicalRegioselectivityIntermolecular forceCatalysisCarbenePhotoredox catalysisCombinatorial chemistryOrganic chemistryMoleculePhotocatalysisN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic C–H Functionalization MethodsRadical Photochemical Reactions