Merging C-H Activation and Strain-Release in Ruthenium-Catalyzed Isoindolinone Synthesis.
Xiao-Qiang HuZi-Kui LiuYe-Xing HouJi-Hang XuYang GaoPublished in: Organic letters (2021)
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.
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