Tian Xianhai, Song Lina, Hashmi A Stephen K
Institut für Organische Chemie, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, 21589, Saudi Arabia.
Angew Chem Int Ed Engl. 2020 Jul 20;59(30):12342-12346. doi: 10.1002/anie.202000146. Epub 2020 Apr 2.
While direct nitrene insertions into C-H bonds have become an important tool for building C-N bonds in modern organic chemistry, the generation of nitrene intermediates always requires transition metals, high temperatures, ultraviolet or laser light. We report a mild synthesis of carbazoles and related building blocks through a visible light-induced intramolecular C-H amination reaction. A striking advantage of this new method is the use of more reactive aryl sulfilimines instead of the corresponding hazardous azides. Different catalysts and divergent light sources were tested. The reaction scope is broad and the product yield is generally high. An efficient gram-scale synthesis of Clausine C demonstrates the applicability and scalability of this new method.
虽然在现代有机化学中，直接将氮宾插入碳氢键已成为构建碳氮键的重要工具，但氮宾中间体的生成总是需要过渡金属、高温、紫外线或激光。我们报道了一种通过可见光诱导的分子内碳氢键胺化反应温和合成咔唑及相关结构单元的方法。这种新方法的一个显著优点是使用了反应活性更高的芳基亚磺酰亚胺，而不是相应的危险叠氮化物。我们测试了不同的催化剂和不同的光源。该反应范围广泛，产物收率一般较高。对克劳斯宁C进行的高效克级合成证明了这种新方法的适用性和可扩展性。
