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

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journal contribution
posted on 16.02.2016, 00:00 by E Tang, Yinjiao Zhao, Wen Li, Weilin Wang, Meng Zhang, Xin Dai
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.