title: Brønsted acid catalyzed monoalkylation of anilines with trichloroacetimidates.
abstract: Trichloroacetimidates are useful alkylating agents for aromatic amines, requiring only a catalytic amount of a Brønsted acid to facilitate the reaction. Monoalkylation predominates under these conditions. Electron-poor anilines provide superior yields, with electron-rich anilines sometimes showing competitive Friedel-Crafts alkylation. A single flask protocol with formation of the imidate in situ is demonstrated, providing a convenient method for the direct substitution of alcohols with anilines. Reaction with a chiral imidate favors a mechanism that proceeds through a carbocation intermediate.
authors.affiliation: Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University , Syracuse, New York 13244, United States.
authors.forename: Daniel R
authors.initials: DR
authors.lastname: Wallach
authors.forename: Patrick C
authors.initials: PC
authors.lastname: Stege
authors.forename: Jigisha P
authors.initials: JP
authors.lastname: Shah
authors.forename: John D
authors.initials: JD
authors.lastname: Chisholm