Electrochemical Oxidation Enables Radical Dearomative Spiroannulation to 2H-Spiro[benzofuran-3,9'-fluoren]-2-one.
作者信息
Yue Yuanyuan, Guo Xiaohui, Zhang Jianhang, Zhang Zhiqiang, Zhang Yilin, Tang Qinghu, Bai Ruopeng, Yi Hong, Liu Jianming
机构信息
Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, P.R. China.
The Institute for Advanced Studies (IAS), Wuhan University, Wuhan, 430072, Hubei, P. R. China.
出版信息
Chemistry. 2024 Aug 1;30(43):e202401303. doi: 10.1002/chem.202401303. Epub 2024 Jul 15.
Developing pragmatic strategies for accessing functional benzofuran-2-ones from 3-([1,1'-biphenyl]-2-yl)benzofuran remains an enduring challenge. Herein, we have achieved a highly discriminating electrochemical oxidative dearomative spiroannulation of 3-([1,1'-biphenyl]-2-yl)benzofuran, culminating in the synthesis of 2H-spiro[benzofuran-3,9'-fluoren]-2-one derivatives. By harnessing the electrophilic intermediates of benzofuryl radical cations supported by DFT calculations, we attain exceptional regioselectivity while eliminating the need for stoichiometric oxidants. Mechanistic investigations reveal a sequence of events involving the benzofuran radical cation, encompassing the capture of HO, nucleophilic arene attack, and subsequent deprotonation, ultimately yielding the final benzofuran-2-ones.
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