Combined Di-tert-butyl Peroxide and Inorganic Base Promoted α-Alkylation of Ethers with Arenesulfonylindoles

The di-tert-butyl peroxide (DTBP) induced coupling of arenesulfonylindoles with ethers such as 1,4-dioxane, tetrahydropyran, tetrahydrofuran, and 1,2-dimethoxyethane was studied. The distinguishing feature of this strategy was characterized by capturing in situ generated vinylogous imine intermediates for the C(sp(3))-H bond alkylation of ethers. This general procedure presents the major advantages of its wide substrate scope and good functional group compatibility