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Abstract <p>A simple method was developed for the preparation of 7-hydroxyimidazo[4,5-<i>b</i>]pyridinium salts via the two-step reaction of readily available 4-amino-1,3-diarylimidazolium salts with 1,3-biselectrophiles in the presence of BF<sub>3</sub>·Et<sub>2</sub>O. The reactivity of the prepared bicyclic compounds was studied through alkylation with various reagents, leading to the synthesis of both <i>O</i>- and <i>N</i>-alkylated derivatives. The applicability of these bicyclic salts as <i>N</i>-heterocyclic carbene (NHC) precursors was demonstrated by their selective C<sup>2</sup>–H metallation, which afforded the corresponding Pd and Au complexes.</p>

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Functionalized Imidazo[4,5-b]pyridinium Salts: Synthesis and Use as M/NHC Precursors

  • 期刊论文

  • 发表日期：

    2026年2月13日

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  • Maxim A. Shevchenko,
  • Konstantin E. Shepelenko,
  • Alexei Yu. Malakhov,
  • Mikhail E. Minyaev,
  • Victor M. Chernyshev

摘要

Abstract

A simple method was developed for the preparation of 7-hydroxyimidazo[4,5-b]pyridinium salts via the two-step reaction of readily available 4-amino-1,3-diarylimidazolium salts with 1,3-biselectrophiles in the presence of BF3·Et2O. The reactivity of the prepared bicyclic compounds was studied through alkylation with various reagents, leading to the synthesis of both O- and N-alkylated derivatives. The applicability of these bicyclic salts as N-heterocyclic carbene (NHC) precursors was demonstrated by their selective C2–H metallation, which afforded the corresponding Pd and Au complexes.