Catalytic Action of Azolium Salts. VIII. Oxidative Aroylation with Arenecarbaldehydes Catalyzed by 1, 3-Dimethylbenzimidazolium Iodide.

…, C ISHIGURO, K IWAMOTO, T HIGASHINO

Index: Miyashita, Akira; Suzuki, Yumiko; Nagasaki, Izuru; Ishiguro, Chie; Iwamoto, Ken-Ichi; Higashino, Takeo Chemical and Pharmaceutical Bulletin, 1997 , vol. 45, # 8 p. 1254 - 1258

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Citation Number: 53

Abstract

Refluxing of a mixture of benzaldehyde (1a), 1, 3-dimethylbenzimidazolium iodide (7), p- nitroaniline (9b) as an oxidizing agent, and 1, 8-diazabicyclo [5, 4, 0]-7-undecene (DBU) in MeOH afforded methyl benzoate (2a) in good yield. Other methyl arenecarboxylates 2 were similarly obtained from arenecarbaldehydes 1. We showed that this aroylation proceeds via the 2-aroyl-1, 3-dimethylbenzimidazolium salt (8). The 1, 2, 4-triazolium salt (18) and the ...