Merging C–H Activation and Strain–Release in Ruthenium-Catalyzed Isoindolinone Synthesis
Xiao‐Qiang Hu, Zi‐Kui Liu, Ye‐Xing Hou, Ji-Hang Xu, Yang Gao
Abstract
The merger of strain-release of 1,2-oxazetidines with carboxylic acid directed C-H activation in catalytic synthesis of isoindolinones is reported for the first time. This reaction opens a new and sustainable avenue to prepare a range of structurally diverse isoindolinone skeletons from readily available benzoic acids. The success of late-stage functionalization of some bioactive acids, and concise synthesis of biologically important skeletons demonstrated its great synthetic potential in drug discovery. Mechanistic studies indicated a plausible C-H activation/β-carbon elimination/intramolecular cyclization cascade pathway.
Topics & Concepts
ChemistryCatalysisIntramolecular forceCombinatorial chemistryBenzoic acidRutheniumDrug discoveryStereochemistryOrganic chemistryBiochemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSynthetic Organic Chemistry Methods