Guo Yu, Wang Ruo-Ya, Kang Jia-Xin, Ma Yan-Na, Xu Cong-Qiao, Li Jun, Chen Xuenian
Henan Key Laboratory of Boron Chemistry and Advanced Energy Materials, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453007, China.
Department of Chemistry, Southern University of Science and Technology, Shenzhen, 518055, China.
Nat Commun. 2021 Oct 13;12(1):5964. doi: 10.1038/s41467-021-25836-5.
Amides are one of the most important organic compounds that are widely applied in medicine, biochemistry, and materials science. To find an efficient synthetic method of amides is a challenge for organic chemistry. We report here a facile synthesis method of primary and secondary amides through a direct amidation of esters with sodium amidoboranes (NaNHRBH, R = H, Me), at room temperature without using catalysts and other reagents. This process is rapid and chemoselective, and features quantitative conversion and wide applicability for esters tolerating different functional groups. The experimental and theoretical studies reveal a reaction mechanism with nucleophilic addition followed by a swift proton transfer-induced elimination reaction.
酰胺是最重要的有机化合物之一，广泛应用于医学、生物化学和材料科学领域。寻找一种高效的酰胺合成方法是有机化学面临的一项挑战。我们在此报告一种通过酯与氨基硼烷钠（NaNHRBH，R = H，Me）直接酰胺化反应，在室温下无需使用催化剂和其他试剂即可简便合成伯酰胺和仲酰胺的方法。该过程快速且具有化学选择性，具有定量转化的特点，并且对耐受不同官能团的酯具有广泛的适用性。实验和理论研究揭示了一种亲核加成后接着快速质子转移引发消除反应的反应机理。
