Kuribara Takahito, Nakajima Masaya, Nemoto Tetsuhiro
Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan.
Org Lett. 2020 Mar 20;22(6):2235-2239. doi: 10.1021/acs.orglett.0c00433. Epub 2020 Mar 2.
In this study, a visible-light-induced intermolecular C-H bond imidation of arenes was achieved at ambient condition. By using simple phthalimide with (diacetoxyiodo)benzene and molecular iodine, direct metal-/photocatalyst-free C-N bond formation was achieved. The imidation protocol was designed by using time-dependent density functional theory calculations and experimentally demonstrated for 28 substrates with as high as 96% yield. Mechanistic studies indicated that radical-mediated aromatic substitution occurred via photolysis of -iodophthalimide under visible-light irradiation.
在本研究中，在环境条件下实现了可见光诱导的芳烃分子间C-H键亚胺化反应。通过使用简单的邻苯二甲酰亚胺与（二乙酰氧基碘）苯和分子碘，实现了无金属/无光催化剂的直接C-N键形成。该亚胺化反应方案通过含时密度泛函理论计算设计，并通过实验证明适用于28种底物，产率高达96%。机理研究表明，在可见光照射下，自由基介导的芳基取代反应通过碘代邻苯二甲酰亚胺的光解发生。
