Facile Synthesis of 3-Aryloxindoles via Br酶nsted Acid Catalyzed Friedel鈥揅rafts Alkylation of Electron-Rich Arenes with 3-Diazooxindoles

详细信息    查看全文

• 作者：Changwei Zhai ; Dong Xing ; Changcheng Jing ; Jun Zhou ; Chengjin Wang ; Dongwei Wang ; Wenhao Hu
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：June 6, 2014
• 年：2014
• 卷：16
• 期：11
• 页码：2934-2937
• 全文大小：295K
• 年卷期：v.16,no.11(June 6, 2014)
• ISSN：1523-7052

文摘

A simple metal-free method for the synthesis of 3-aryloxindoles via Br酶nsted acid catalyzed aromatic C鈥揌 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鈥揅rafts-type alkylation of arenes.