Liu Yao, Li Ji-Lin, Liu Xu-Ge, Wu Jia-Qiang, Huang Zhi-Shu, Li Qingjiang, Wang Honggen
Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.
Org Lett. 2021 Mar 5;23(5):1891-1897. doi: 10.1021/acs.orglett.1c00309. Epub 2021 Feb 16.
Borylated aza-arenes are of great importance in the area of organic synthesis. A radical borylative cyclization of isocyanoarenes with N-heterocyclic carbene borane (NHC-BH) under metal-free conditions was developed. The reaction allows the efficient assembly of several types of borylated aza-arenes (phenanthridines, benzothiazoles, etc.), which are difficult to access using alternative methods. Mild reaction conditions, a good functional-group tolerance, and generally good efficiencies were observed. The utility of these products is demonstrated, and the mechanism is discussed.
硼化氮杂芳烃在有机合成领域具有重要意义。已开发出一种在无金属条件下异氰基芳烃与氮杂环卡宾硼烷（NHC-BH）的自由基硼化环化反应。该反应能够高效组装多种类型的硼化氮杂芳烃（菲啶、苯并噻唑等），而这些用其他方法难以获得。反应条件温和，官能团耐受性良好，且效率普遍较高。展示了这些产物的实用性，并对反应机理进行了讨论。
