Concise synthesis of 2,3-disubstituted quinoline derivatives via ruthenium-catalyzed three-component deaminative coupling reaction of anilines, aldehydes and amines
Concise synthesis of 2,3-disubstituted quinoline derivatives via ruthenium-catalyzed three-component deaminative coupling reaction of anilines, aldehydes and amines
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DOI：
10.1039/d3ob00348e
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发表时间：
2023-04-06
影响因子：
3.2
通讯作者：
Yi，Chae S.
中科院分区：
文献类型：
--
作者：
Shakenov，Aldiyar;Gnyawali，Krishna Prasad;Yi，Chae S.
Ru-H 络合物 (PCy3)2(CO)RuHCl (1) 被发现是一种高效催化剂，可用于苯胺与醛和烯丙胺的三组分脱氨偶联反应，形成 2,3-二取代喹啉产物。苯胺与醛和环状烯胺的类似偶联反应导致选择性形成三环喹啉衍生物。反应谱研究表明，亚胺最初是由苯胺和醛脱水偶联形成的，然后与胺底物发生脱氨基偶联和环化反应，形成喹啉产物。催化偶联方法提供了2,3-二取代喹啉衍生物的一步有效合成，无需使用任何反应试剂或形成浪费的副产物。
The Ru–H complex (PCy3)2(CO)RuHCl (1) was found to be a highly effective catalyst for the three-component deaminative coupling reaction of anilines with aldehydes and allylamines to form 2,3-disubstituted quinoline products. The analogous coupling reaction of anilines with aldehydes and cyclic enamines led to the selective formation of the tricyclic quinoline derivatives. The reaction profile study showed that the imine is initially formed from the dehydrative coupling of aniline and aldehyde, and it undergoes the deaminative coupling and annulation reaction with amine substrate to form the quinoline product. The catalytic coupling method provides a step-efficient synthesis of 2,3-disubstituted quinoline derivatives without employing any reactive reagents or forming wasteful byproducts.