Iron-catalyzed one-pot synthesis of benzimidazoles from 2-nitroanilines and benzylic alcohols

Tetrahedron Letters

Volumn 54, Issue 50, 2013, Pages 6934-6936

  Li, Gang ^a   Wang, Jin ^a   Yuan, Baokun ^a   Zhang, Dongfeng ^a   Lin, Ziyun ^a   Li, Peng ^a   Huang, Haihong ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Benzimidazole; Dppf; Hydrogen transfer; One pot synthesis

Indexed keywords

ANILINE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; BENZYL ALCOHOL; IRON DERIVATIVE; TOLUENE DERIVATIVE;

ALCOHOL OXIDATION; AROMATIZATION; ARTICLE; CATALYSIS; CYCLIZATION; DEHYDROGENATION; ONE POT SYNTHESIS; REDUCTION (CHEMISTRY); TEMPERATURE MEASUREMENT;

EID: 84902552683     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.10.045     Document Type: Article

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21. General procedure: The preparation of 2-phenyl-1H-benzoimidazole (3a): A 15 mL capped tube was charged with 2-nitroaniline (0.36 mmol), benzyl alcohol (0.094 mL, 0.90 mmol) and dppf (0.018 mmol). The tube was flushed with argon for 10 min. Then the degassed toluene (3 mL) was added. The tube was flushed with argon, capped, and heated at 150 °C for 24 h. After cooling to room temperature, the reaction mixture was then concentrated in vacuo, and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 4:1) to afford the pure 3a as a white solid. The product was identified by NMR and MS and the data are identical to the reported values.
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