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Facile Synthesis of 3‑Aryloxindoles via Brønsted Acid Catalyzed Friedel–Crafts Alkylation of Electron-Rich Arenes with 3‑Diazooxindoles

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journal contribution
posted on 2014-06-06, 00:00 authored by Changwei Zhai, Dong Xing, Changcheng Jing, Jun Zhou, Chengjin Wang, Dongwei Wang, Wenhao Hu
A simple metal-free method for the synthesis of 3-aryloxindoles via Brønsted acid catalyzed aromatic C–H functionalization of electron-rich arenes with 3-diazooxindoles is developed. In the presence of a catalytic amount of TfOH, a series of 3-aryloxindoles are synthesized as single regioisomers in good to excellent yields. This transformation is proposed to proceed through acid-catalyzed protonation of 3-diazooxindoles into diazonium ions followed by Friedel–Crafts-type alkylation of arenes.