Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 357, Issue 13, Pages 2951-2956Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201500302
Keywords
aerobic oxidative cyclization; benzimidazole-substituted boronic acids; iodides; N-methyliminodiacetic acid (MIDA); MIDA boronates; Suzuki-Miyaura coupling reaction
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Funding
- National Research Foundation of Korea (NRF) - Korean Government [NRF-2013R1A1A1008434, NRF-20100020209]
- NRF [NRF-2014M2A84021398]
- National Research Foundation of Korea [2013R1A1A1008434, 2012M2A8A4025895, 2010-0020209] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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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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