Mahato Sanjit K, Chatani Naoto
Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
J Org Chem. 2022 Jun 17;87(12):8183-8193. doi: 10.1021/acs.joc.2c00949. Epub 2022 Jun 6.
The Ir(III)-catalyzed C-H amidation of 2-aroylimidazoles with 3-aryldioxazolones as an amidating reagent is reported. The method provides a broad substrate scope with wide functional group compatibility. Mechanistic studies indicate that C-H bond cleavage is reversible and appears not to be the rate-determining step. The presence of an electron-donating group in the 2-aroylimidazoles and an electron-withdrawing group in the 3-aryldioxazoles significantly accelerates the reaction, suggesting that nitrene insertion is the rate-determining step.
报道了以3-芳基二恶唑酮作为酰胺化试剂，铱(III)催化2-芳酰基咪唑的C-H酰胺化反应。该方法具有广泛的底物范围和良好的官能团兼容性。机理研究表明，C-H键的断裂是可逆的，似乎不是反应的速率决定步骤。2-芳酰基咪唑中供电子基团和3-芳基二恶唑中吸电子基团的存在显著加速了反应，这表明氮宾插入是反应的速率决定步骤。
