Synthesis of Benzimidazole-Substituted Arylboronic Acids via Aerobic Oxidation of 1,2-Arylenediamines and Formyl-Substituted Aryl MIDA Boronates using Potassium Iodide as a Catalyst

Ye Sol Lee, Cheol-Hong Cheon

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A highly efficient protocol for the synthesis of benzimidazole-substituted arylboronic acids was developed via aerobic oxidative cyclization of 1,2-aryldiamines and formyl-substituted aryl MIDA (N-methyliminodiacetic acid) boronates using potassium iodide as a nucleophilic catalyst. Furthermore, a one-pot protocol for the synthesis of benzimidazole-substituted arylboronic acids from 1,2-phenylenediamines and formyl-substituted arylboronic acids was developed without the isolation of any intermediates. The resulting boronic acids were further subjected to Suzuki-Miyaura coupling reactions without isolation, leading to diaryl-substituted benzimidazoles with only one separation step.

Original languageEnglish
Pages (from-to)2951-2956
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume357
Issue number13
DOIs
Publication statusPublished - 2015 Sep 1

Fingerprint

Potassium iodide
Potassium Iodide
Oxidation
Catalysts
Acids
Benzimidazoles
Boronic Acids
Cyclization
N-methyliminodiacetic acid
benzimidazole

Keywords

  • aerobic oxidative cyclization
  • benzimidazole-substituted boronic acids
  • iodides
  • MIDA boronates
  • N-methyliminodiacetic acid (MIDA)
  • Suzuki-Miyaura coupling reaction

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

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T1 - Synthesis of Benzimidazole-Substituted Arylboronic Acids via Aerobic Oxidation of 1,2-Arylenediamines and Formyl-Substituted Aryl MIDA Boronates using Potassium Iodide as a Catalyst

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AU - Cheon, Cheol-Hong

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N2 - A highly efficient protocol for the synthesis of benzimidazole-substituted arylboronic acids was developed via aerobic oxidative cyclization of 1,2-aryldiamines and formyl-substituted aryl MIDA (N-methyliminodiacetic acid) boronates using potassium iodide as a nucleophilic catalyst. Furthermore, a one-pot protocol for the synthesis of benzimidazole-substituted arylboronic acids from 1,2-phenylenediamines and formyl-substituted arylboronic acids was developed without the isolation of any intermediates. The resulting boronic acids were further subjected to Suzuki-Miyaura coupling reactions without isolation, leading to diaryl-substituted benzimidazoles with only one separation step.

AB - A highly efficient protocol for the synthesis of benzimidazole-substituted arylboronic acids was developed via aerobic oxidative cyclization of 1,2-aryldiamines and formyl-substituted aryl MIDA (N-methyliminodiacetic acid) boronates using potassium iodide as a nucleophilic catalyst. Furthermore, a one-pot protocol for the synthesis of benzimidazole-substituted arylboronic acids from 1,2-phenylenediamines and formyl-substituted arylboronic acids was developed without the isolation of any intermediates. The resulting boronic acids were further subjected to Suzuki-Miyaura coupling reactions without isolation, leading to diaryl-substituted benzimidazoles with only one separation step.

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KW - Suzuki-Miyaura coupling reaction

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