Brønsted acid catalyzed monoalkylation of anilines with trichloroacetimidates

Daniel R. Wallach, Patrick C. Stege, Jigisha P. Shah, John D. Chisholm

Research output: Contribution to journalArticle

20 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1993-2000
Number of pages8
JournalJournal of Organic Chemistry
Volume80
Issue number3
DOIs
StatePublished - Feb 6 2015

ASJC Scopus subject areas

  • Organic Chemistry

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