Transition‐Metal‐Free Synthesis of 1,2‐diphenyl‐1H‐benzo[d] Imidazole Derivatives from N‐phenylbenzimidamides and Cyclohexanones

A transition‐metal‐free strategy for the formation of 1,2‐diphenyl‐1H‐benzo[d] imidazoles from N‐phenylbenzimidamides and cyclohexanones is introduced. This is the first report on the direct synthesis of 1,2‐diphenyl‐1H‐benzo[d] imidazoles from cyclohexanones and N‐phenylbenzimidamides via iodine‐ p...

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Veröffentlicht in:Advanced synthesis & catalysis 2020-02, Vol.362 (3), p.487-492
Hauptverfasser: Lu, Guoqiang, Luo, Nan, Hu, Fangpeng, Ban, Zihui, Zhan, Zhenzhen, Huang, Guo‐Sheng
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Sprache:eng
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Zusammenfassung:A transition‐metal‐free strategy for the formation of 1,2‐diphenyl‐1H‐benzo[d] imidazoles from N‐phenylbenzimidamides and cyclohexanones is introduced. This is the first report on the direct synthesis of 1,2‐diphenyl‐1H‐benzo[d] imidazoles from cyclohexanones and N‐phenylbenzimidamides via iodine‐ promoted oxidative cyclization. Non‐aromatic cyclohexanones were smoothly dehydrogenated, and acted as an aryl source using oxygen as a green oxidant. The catalytic use of iodine makes this method quite simple, more economical and convenient. Under optimized conditions, various substituted 1,2‐diphenyl‐1H‐benzo[d] imidazoles were smoothly reacted, and the desired substituted imidazoles were generated with moderate to excellent yields.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201901161