Tang E1, Zhao Y1, Li W1, Wang W1, Zhang M1, Dai X1.
Org Lett. 2016 Mar 4;18(5):912-5. doi: 10.1021/acs.orglett.5b03579. Epub 2016 Feb 16.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.