Cis-difluoromethyl hetarylative dearomatization by a radical docking-migration cascade
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Updated: Jan 11, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
Jie Wang1,2, Hao Kang1, Shan Yang1
1Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, State Key Laboratory of Synergistic Chem-Bio Synthesis, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University 800 Dongchuan Road Shanghai 200240 China chzhu@sjtu.edu.cn chenxiangyang@sjtu.edu.cn.
Abstract:
Despite the significant advances in dearomatization reactions, the challenge of achieving uncyclized dearomatization to produce thermodynamically unstable 1,2-cis-products remains unresolved. Here, we present a novel approach for uncyclized cis-selective dearomatization reaction via a radical docking-migration cascade. The reaction proceeds under mild photochemical conditions, simultaneously incorporating a CF2H and a hetaryl group into indoline backbones. A wide range of indoles with diverse functional groups are compatible with the reaction. Furthermore, this method is also suitable for the dearomatization of benzothiophenes, furans, thiophenes and a few polycyclic aromatic hydrocarbons. This protocol features excellent selectivities, broad product diversity, and does not require photosensitizers. DFT calculations rationalize the observed regioselectivities for various heteroarenes and cis-stereoselectivities.
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