Palladium-catalyzed C–H activation of simple arenes and cascade reaction with nitriles: access to 2,4,5-trisubstituted oxazoles
Ling Dai, Shuling Yu, Yinlin Shao, Renhao Li, Zhongyan Chen, Ningning Lv, Jiuxi Chen
Abstract
An efficient and straightforward protocol for the assembly of the pharmaceutically and biologically valuable oxazole skeleton is achieved for the first time from readily available simple arenes and functionalized aliphatic nitriles. This transformation involves palladium-catalyzed C-H activation, carbopalladation and a tandem annulation sequence in one pot. Notably, the reaction proceeds efficiently under redox-neutral conditions, and exhibits high atom-economy. Deuterium-labeling experiments suggested that C-H bond cleavage of the simple arenes might be the rate-determining step.
Topics & Concepts
AnnulationOxazolePalladiumChemistryCatalysisTandemCombinatorial chemistryCascade reactionCascadeSequence (biology)Organic chemistryMaterials scienceBiochemistryComposite materialChromatographyCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCatalytic Cross-Coupling Reactions