Faye Youssou, Rkein Batoul, Bigot Antoine, Lequeux Thierry, Legros Julien, Chataigner Isabelle
Univ Rouen Normandie, INSA Rouen Normandie, CNRS, Normandie Univ, COBRA, 76000, Rouen, France.
Normandie Univ., ENSICAEN, Unicaen, CNRS, LCMT, 14000, Caen, France.
Chemistry. 2023 Sep 1;29(49):e202301567. doi: 10.1002/chem.202301567. Epub 2023 Jul 27.
The photocatalyzed dearomative reaction between various electron-deficient aromatic compounds and a non-stabilized azomethine ylide is successfully performed in a flow system. Whereas the use of supported eosin as organic photocatalyst exhibits limited efficiency, turning to the soluble Rose Bengal allows to transform a broad range of substrates from hetarenes (indole, benzofuran, quinoline, pyridine) to naphthalenes and benzenes. This photocatalyzed (3+2) dearomative cycloaddition under green light irradiation provides a simple and efficient access to tridimensional pyrrolidino scaffolds with a tetrasubstituted carbon center at ring junction and can be performed in the friendly ethyl acetate. Computational studies support the mechanism involving azomethine ylide as reactive species toward the electron-poor arene.
在流动体系中成功实现了各种缺电子芳香化合物与非稳定甲亚胺叶立德之间的光催化去芳构化反应。尽管使用负载型曙红作为有机光催化剂效率有限，但改用可溶性玫瑰红则可以将多种底物从杂芳烃（吲哚、苯并呋喃、喹啉、吡啶）转化为萘和苯。这种在绿光照射下的光催化（3+2）去芳构化环加成反应提供了一种简单有效的方法来合成在环连接处具有四取代碳中心的三维吡咯烷支架，并且可以在友好的乙酸乙酯中进行。计算研究支持了该反应机理，即甲亚胺叶立德作为对缺电子芳烃具有反应活性的物种。
