4.8 Article

A Modular Synthesis of Highly Substituted Imidazolium Salts

Journal

ORGANIC LETTERS
Volume 11, Issue 4, Pages 1019-1022

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol8029609

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Funding

  1. Deutsche Forschungsgemeinschaft
  2. Fonds der Chemischen Industrie
  3. Deutsche Akademische Austauschdiens
  4. Alexander von Humboldt Foundation
  5. Alfried Krupp von Bohlen and Halbach Foundation

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A versatile and modular one-pot method for the preparation of differently substituted symmetrical and unsymmetrical imidazolium salts is reported, and 19 examples are given. In the key step, readily available formamidines and alpha-halo ketones are coupled to give imidazolinium salts 3, followed by imidazolium salt formation by acylation-induced elimination. For many substitution patterns of the imidazolium salt products, this efficient strategy compares favorably with well-known processes in terms of yield, ease of synthesis, and robustness.

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