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Synthesis of Biquinolines via a Pd‐Catalyzed Borylation Reaction
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-08-10 , DOI: 10.1002/ajoc.202000356
Shiv S. Gupta 1 , Krishna K. Sharma 1 , Manoj Prajapati 1 , Gajanan K. Rathod 1 , Rahul Jain 1
Affiliation  

Synthesis of biquinolines starting from easily available haloquinolines via a Pd‐catalyzed borylation reaction in the presence of inexpensive bis(pinacolato)diboron is described. The reaction involves Pd(dppf)Cl2 ⋅ CH2Cl2‐catalyzed cross‐coupling of haloquinolines with bis(pinacolato)diboron to afford in situ generated heteroarylboronates. The intermediate heteroarylboronates immediately undergoes homocoupling to afford biquinolines in good to excellent yields in short reaction time. The scope of the reaction was demonstrated by its successful extension to structurally related N‐heterocycles.

中文翻译:

通过Pd催化的硼氢化反应合成联喹啉

描述了在廉价的双(频哪醇)二硼烷存在下,通过Pd催化的硼化反应,从易于获得的卤代喹啉开始合成联喹啉。该反应涉及Pd(dppf)Cl 2  ·CH 2 Cl 2催化的卤代喹啉与双(频哪醇)二硼烷的交叉偶联,以提供原位生成的杂芳基硼酸酯。中间体杂芳基硼酸酯立即进行均偶联,从而在短的反应时间内以良好的收率获得优异的联喹啉。反应范围成功地扩展到与结构相关的N-杂环,证明了反应的范围。
更新日期:2020-10-11
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