Catalytic Selenium-Promoted Intermolecular Friedel–Crafts Alkylation with Simple Alkenes

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• 作者：E Tang ; Yinjiao Zhao ; Wen Li ; Weilin Wang ; Meng Zhang ; Xin Dai
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：March 4, 2016
• 年：2016
• 卷：18
• 期：5
• 页码：912-915
• 全文大小：443K
• ISSN：1523-7052

文摘

A method for conducting selenium-promoted intermolecular Friedel–Crafts (F–C) alkylation reactions has been developed with simple alkenes using trimethylsilyl trifluoromethanesulfonate as a catalyst and N-phenylselenophthalimide as an efficient selenium source. Electron-rich arenes smoothly underwent F–C alkylation with a variety of alkenes to afford alkylated products in good yield and with high regioselectivity and diastereoselectivity. The regioselectivity and stereoselectivity of arenes and alkenes as well as a preliminary mechanism of the F–C alkylation reaction are discussed.