Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
J Am Chem Soc. 2022 May 25;144(20):8902-8907. doi: 10.1021/jacs.2c02922. Epub 2022 May 12.
A catalytic approach to intercept the transient HNO for a chemoselective primary amination of arylboronic acids is reported. A phosphetane-based catalyst operating within P/P═O redox cycling is shown to capture HNO, generated in situ by Nef decomposition of 2-nitropropane, to selectively install the primary amino group at aryl C centers. The method furnishes versatile primary arylamines from arylboronic acid substrates with the preservation of otherwise reactive functional groups.
本文报道了一种催化方法，可以拦截瞬态 HNO，从而实现芳基硼酸的选择性伯胺化反应。实验结果表明，基于膦杂环戊二烯的催化剂在 P/P═O 氧化还原循环中起作用，可以捕获由 2-硝基丙烷的 Nef 分解原位生成的 HNO，从而选择性地在芳基 C 中心上安装伯氨基。该方法可以从芳基硼酸底物中获得多功能的伯芳基胺，同时保留其他反应性官能团。
