NNN-Ruthenium Catalysts for the Synthesis of Pyridines, Quinolines, and Pyrroles by Acceptorless Dehydrogenative Condensation,Organometallics

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NNN-Ruthenium Catalysts for the Synthesis of Pyridines, Quinolines, and Pyrroles by Acceptorless Dehydrogenative Condensation
Organometallics ( IF 2.5 ) Pub Date : 2018-07-11 , DOI: 10.1021/acs.organomet.8b00359
Danfeng Deng ₁ , Bowen Hu ₁ , Min Yang ₁ , Dafa Chen ₁

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The bidentate ruthenium complex (HO-C₅H₃N-CO-C₅H₃N-C₅H₄N)Ru(CO)₂Cl₂ (2) could transform to a tridentate product (HO-C₅H₃N-CO-C₅H₃N-C₅H₄N)Ru(CO)Cl₂ (3), which further reacted with CH₃ONa in the presence of PPh₃ to convert to two complexes [(OC₅H₃N-CO-C₅H₃N-C₅H₄N)Ru(PPh₃)₂(CO)]Cl^– (4) and [(OC₅H₃N-CO-C₅H₃N-C₅H₄N)Ru(PPh₃)(CO)Cl] (5), via −OH deprotonation. The catalytic coupling cyclizations of secondary alcohols with amino alcohols were investigated, and complex 3 exhibited the highest activity. The coupling reactions proceeded in air with only 0.2 mol % catalyst loading and had a broad scope for the synthesis of pyridines, quinolones, and pyrroles.

中文翻译：

NNN-钌催化剂，通过无受体脱氢缩合反应合成吡啶，喹啉和吡咯

双齿钌配合物（HO-C ₅ H ₃ N-CO-C ₅ H ₃ N-C ₅ H ₄ N）Ru（CO）₂ Cl ₂（2）可以转变为三齿产物（HO-C ₅ H ₃ N- CO-C ₅ H ₃ N-C ₅ H ₄ N）Ru（CO）Cl ₂（3），其在PPh ₃存在下进一步与CH ₃ ONa反应，转化为两种络合物[（OC ₅ H ₃ N-CO- C ₅高₃NC ₅ H ₄ N）Ru（PPh ₃）₂（CO）] Cl ^–（4）和[（OC ₅ H ₃ N-CO-C ₅ H ₃ N-C ₅ H ₄ N）Ru（PPh ₃）（CO） Cl]（5），通过-OH去质子化。研究了仲醇与氨基醇的催化偶合环化反应，并且配合物3表现出最高的活性。偶联反应在空气中仅以0.2 mol％的催化剂负载量进行，并具有广泛的吡啶，喹诺酮和吡咯的合成范围。

更新日期：2018-07-12

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