Shakenov Aldiyar, Gnyawali Krishna Prasad, Yi Chae S
Department of Chemistry, Marquette University, Milwaukee, Wisconsin 53233, USA.
Org Biomol Chem. 2023 May 3;21(17):3582-3587. doi: 10.1039/d3ob00348e.
The Ru-H complex (PCy)(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.
已发现Ru-H配合物(PCy)(CO)RuHCl (1)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基偶联反应，以形成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。反应历程研究表明，亚胺最初由苯胺和醛的脱水偶联形成，然后与胺底物发生脱氨基偶联和环化反应，形成喹啉产物。该催化偶联方法提供了一种步骤高效的2,3-二取代喹啉衍生物合成方法，无需使用任何活性试剂或形成浪费的副产物。
