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