Opie Christopher R, Noda Hidetoshi, Shibasaki Masakatsu, Kumagai Naoya
Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
Graduate School of Pharmaceutical Sciences, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan.
Org Lett. 2023 Feb 3;25(4):694-697. doi: 10.1021/acs.orglett.2c04382. Epub 2023 Jan 20.
Diboron substructures have emerged as a promising scaffold for the catalytic dehydrative amidation of carboxylic acids and amines. This Letter describes the design, synthesis, and evaluation of the first isolable N(BOH) compound as an amidation catalyst. The new catalyst outperforms the previously reported BNO heterocycle catalyst, with respect to turnover frequency, albeit the former gradually decomposes upon exposure to amines. This work opens up an avenue for designing a better catalyst for direct amidation.
二硼亚结构已成为用于羧酸和胺的催化脱水酰胺化反应的一种有前景的骨架。本通讯报道了首例可分离的N(BOH)化合物作为酰胺化催化剂的设计、合成及评估。尽管新催化剂在暴露于胺时会逐渐分解，但就周转频率而言，其性能优于先前报道的BNO杂环催化剂。这项工作为设计更好的直接酰胺化催化剂开辟了一条途径。
