Zhu Yun-Long, Dong Yi-Fan, Wang Si-Ru, Li You-Gui, Wu Xiang, Ye Long-Wu
School of Chemistry and Chemical Engineering, Hefei University of Technology, 193 Tunxi Road, Hefei 230009, China.
State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.
Org Lett. 2024 Jan 26;26(3):631-635. doi: 10.1021/acs.orglett.3c03856. Epub 2024 Jan 12.
A gold-catalyzed, nucleophile-controlled cascade reaction of -(2-azidophenyl-ynyl)methanesulfonamides with nitriles and water is described that provides structurally diverse 5-pyrimido[5,4-]indoles and 2-benzylidene-3-indolinones in good to excellent yields. Mechanistic studies indicate that the β-sulfonamido-α-imino gold carbene is the key intermediate which is generated through the gold-catalyzed cyclization of -(2-azidophenyl-ynyl)methanesulfonamides and undergoes formal [4 + 2] cascade annulation with nitriles and intramolecular S2' type reaction with water, respectively.
描述了一种金催化的、亲核试剂控制的 -(2-叠氮基苯基乙炔基)甲磺酰胺与腈和水的串联反应，该反应能以良好至优异的产率提供结构多样的 5-嘧啶并[5,4-]吲哚和 2-亚苄基-3-吲哚酮。机理研究表明，β-磺酰胺基-α-亚氨基金卡宾是关键中间体，它通过金催化的 -(2-叠氮基苯基乙炔基)甲磺酰胺环化反应生成，分别与腈进行形式上的 [4 + 2] 串联环化反应以及与水进行分子内 S2' 型反应。
