Carbene Bridging C–H Activation: Facile Isocoumarin Synthesis Through Palladium‐Catalyzed Reaction of 2‐Pseudohalobenzaldehydes with Aryl Diazoesters
Chao Yan, Yinghua Yu, Bo Peng, Xueliang Huang
Abstract
A reaction mode on carbene bridging C–H activation (CBA) is described. In this reaction, metal carbene was produced prior to the event of C–H bond metallation. Readily available aryl dizaoesters were employed as the carbene precursors. Migratory insertion of the palladium carbene intermediate could create a modular bridging arm to promote the C–H bond palladation of tethered aldehyde moiety. Its synthetic potential was demonstrated by facile construction isocoumarin scaffold from easily accessible starting materials. Furthermore, this protocol is also amenable for late‐functionalization of complex molecules.
Topics & Concepts
CarbeneChemistryMoietyArylIsocoumarinPalladiumMigratory insertionCombinatorial chemistryAldehydeSynthonCatalysisStereochemistryOrganic chemistryAlkylCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions