Photoredox-Catalyzed Carbamoyl Radical-Initiated Dearomative Spirocyclization To Access Spiro-Cyclohexadiene Oxindoles
Chunhua Ma, Qing Guo, Hui Meng, Shengnan Yan, Qingjie Ding, Yuqin Jiang, Bing Yu
Abstract
The sustainable construction of spirocyclic compounds is important to the scientific community and the pharmaceutical industries. Herein, we demonstrate a carbamoyl radical-initiated intramolecular dearomative spirocyclization to access the spiro-cyclohexadiene oxindoles under visible light irradiation, which constitutes the first example of accessing the I-substituted derivatives that facilitate diversified transformations. Additionally, the scalability, late-stage modification of drugs, and significant antitumor activity of the products demonstrate the novel spirocyclic synthesis platform for expediting drug development.
Topics & Concepts
ChemistryCatalysisCombinatorial chemistryPhotoredox catalysisMedicinal chemistryPhotochemistryOrganic chemistryPhotocatalysisCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsRadical Photochemical Reactions