NDLI: Dehydrogenative synthesis of benzimidazoles under mild conditions with supported iridium catalysts

Content Provider	Royal Society of Chemistry (RSC)
Author	Abe, Ryu Hosokawa, Saburo Inoue, Masashi Miura, Hiroki Tateyama, Keisuke Wada, Kenji
Copyright Year	2016
Abstract	Solid supported iridium catalysts, which show excellent activity for the dehydrogenative synthesis of benzimidazoles from primary alcohols and phenylenediamine derivatives under mild reaction conditions, were developed. Among the catalysts examined, the titania-supported iridium catalyst showed the highest activity, and benzimidazole derivatives were selectively produced at temperatures of 80 °C or higher. For example, the reaction of phenylenediamine (1a) with benzyl alcohol (2a) in the presence of Ir(1.0 wt%)/TiO2 (1.0 mol%, towards 1a) at 120 °C selectively gave 2-phenylbenzimidazole (3aa) in 80% yield after 6 h and over 90% yield after 18 h. A high turnover number (TON) of more than 800 was achieved in the reaction at a higher substrate-to-catalyst ratio. Reduction of the catalysts under a hydrogen atmosphere at around 500 to 600 °C is essential for their significant activity. Characterization of the catalysts by gas adsorption, XRD, XPS, H2-TPR, TEM, and XAFS techniques revealed that highly-dispersed nanoparticles of the iridium(0) species (ca. 1 to 2 nm in diameter) formed on TiO2 are responsible for the catalysis. The catalysts could be recycled without a significant loss of activity, and the leaching of the iridium species into the solution during the catalytic runs was negligible, which suggests that the present catalysts would be excellent from both environmental and practical perspectives.
Starting Page	1677
Ending Page	1684
Page Count	8
File Format	HTM / HTML PDF
ISSN	20444753
Volume Number	6
Issue Number	6
Journal	Catalysis Science & Technology
DOI	10.1039/c5cy01601k
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	X-ray crystallography Phenylenediamine Transmission electron microscopy Adsorption Hydrogen Benzimidazole Iridium Benzyl alcohol Turnover number
Content Type	Text
Resource Type	Article
Subject	Catalysis

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