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Nickel–PNN catalysed sustainable synthesis of polysubstituted quinolines under microwave irradiation
Catalysis Science & Technology ( IF 4.4 ) Pub Date : 2024-08-20 , DOI: 10.1039/d4cy00863d Manali A. Mohite 1 , Sonu Sheokand 1 , Maravanji S. Balakrishna 1
Catalysis Science & Technology ( IF 4.4 ) Pub Date : 2024-08-20 , DOI: 10.1039/d4cy00863d Manali A. Mohite 1 , Sonu Sheokand 1 , Maravanji S. Balakrishna 1
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In this manuscript, the synthesis of a series of cationic NiII complexes based on mixed donor triazolyl-pyridine-based aminophosphine, [(NiCl){R′PRNN}-κ3-P,N,N]OTf (R = H or Me; R′ = Ph or tBu), is described. The neutral dearomatized complexes [(NiCl){R′PNN}-κ3-P,N,N] (R′ = Ph or tBu) were prepared by deprotonation of [(NiCl){PPhN(H)N}-κ3-P,N,N]OTf (Ni1) and [(NiCl){(tBu2P)N(H)N}-κ3-P,N,N]OTf (Ni3) with 1 equiv. of tBuOK. These complexes (0.5 mol%) were employed for the synthesis of substituted quinolines at 110 °C under microwave irradiation with 20 mol% of KOH. Among these, complexes [(NiCl){tBuPHNN-κ3-P,N,N}]OTf (Ni3) and [(NiCl){tBuPNN}-κ3-P,N,N] (Ni5) were found to be highly efficient. A wide range of derivatives, including aryl, aliphatic, acyclic ketones, primary alcohols and aminobenzyl alcohols, yielded the corresponding quinolines in good to excellent yields (62 examples). A series of control experiments were carried out to establish the reaction mechanism. HR-MS spectral studies were investigated to characterize the nickel-hydride intermediate. Mechanistic studies confirmed that the reaction takes an acceptorless dehydrogenative coupling pathway.
中文翻译:
微波辐射下镍-PNN催化多取代喹啉的可持续合成
在这篇手稿中,基于混合供体三唑基-吡啶基氨基膦合成了一系列阳离子 Ni II配合物,[(NiCl){ R′ P R NN}-κ 3 -P,N,N]OTf (R =描述了H或Me;R'=Ph或tBu )。通过 [(NiCl){P Ph N(H)N} 去质子化制备中性脱芳构化配合物 [(NiCl){ R' PNN}-κ 3 -P,N,N] (R' = Ph 或t Bu) -κ 3 -P,N,N]OTf ( Ni1 ) 和 [(NiCl){( t Bu 2 P)N(H)N}-κ 3 -P,N,N]OTf ( Ni3 ) 具有 1 当量。 t BuOK。这些配合物 (0.5 mol%) 用于在 110 °C 微波辐射下用 20 mol% KOH 合成取代喹啉。其中,配合物 [(NiCl){ t Bu P H NN-κ 3 -P,N,N}]OTf ( Ni3 ) 和 [(NiCl){ t Bu PNN}-κ 3 -P,N,N] ( Ni5 )被发现非常高效。 多种衍生物,包括芳基、脂肪族、无环酮、伯醇和氨基苄醇,以良好到优异的产率产生相应的喹啉(62个实例)。进行了一系列控制实验来建立反应机理。研究 HR-MS 光谱研究来表征氢化镍中间体。机理研究证实该反应采用无受体脱氢偶联途径。
更新日期:2024-08-20
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
微波辐射下镍-PNN催化多取代喹啉的可持续合成
在这篇手稿中,基于混合供体三唑基-吡啶基氨基膦合成了一系列阳离子 Ni II配合物,[(NiCl){ R′ P R NN}-κ 3 -P,N,N]OTf (R =描述了H或Me;R'=Ph或tBu )。通过 [(NiCl){P Ph N(H)N} 去质子化制备中性脱芳构化配合物 [(NiCl){ R' PNN}-κ 3 -P,N,N] (R' = Ph 或t Bu) -κ 3 -P,N,N]OTf ( Ni1 ) 和 [(NiCl){( t Bu 2 P)N(H)N}-κ 3 -P,N,N]OTf ( Ni3 ) 具有 1 当量。 t BuOK。这些配合物 (0.5 mol%) 用于在 110 °C 微波辐射下用 20 mol% KOH 合成取代喹啉。其中,配合物 [(NiCl){ t Bu P H NN-κ 3 -P,N,N}]OTf ( Ni3 ) 和 [(NiCl){ t Bu PNN}-κ 3 -P,N,N] ( Ni5 )被发现非常高效。 多种衍生物,包括芳基、脂肪族、无环酮、伯醇和氨基苄醇,以良好到优异的产率产生相应的喹啉(62个实例)。进行了一系列控制实验来建立反应机理。研究 HR-MS 光谱研究来表征氢化镍中间体。机理研究证实该反应采用无受体脱氢偶联途径。