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The Rational Design and Synthesis of Water-Soluble Thiourea Ligands for Recoverable Pd-Catalyzed Aerobic Aqueous Suzuki–Miyaura Reactions at Room Temperature
Synthesis ( IF 2.2 ) Pub Date : 2018-01-04 , DOI: 10.1055/s-0036-1589150
Wei Chen 1 , Xiao-Yan Lu 2 , Bei-Hua Xu 1 , Wei-guo Yu 1 , Zi-niu Zhou 1 , Ying Hu 1
Affiliation  

Abstract

Eight precatalysts containing carboxylic-functionalized thiourea ligands are prepared and their activities and recyclability are evaluated in aerobic aqueous Suzuki–Miyaura reactions. A bulky monothiourea–Pd complex, functionalized with four carboxylic groups, shows the best activity and recyclability in the coupling of aryl bromides with arylboronic acids. The catalyst can be reused at least five times without any significant reduction in its catalytic activity. TEM analysis and the confirmed catalytic activity of the observed black precipitate reveal that Pd nanoparticles are formed during the reactions and are stabilized by the carboxylic-functionalized thiourea ligands.

Eight precatalysts containing carboxylic-functionalized thiourea ligands are prepared and their activities and recyclability are evaluated in aerobic aqueous Suzuki–Miyaura reactions. A bulky monothiourea–Pd complex, functionalized with four carboxylic groups, shows the best activity and recyclability in the coupling of aryl bromides with arylboronic acids. The catalyst can be reused at least five times without any significant reduction in its catalytic activity. TEM analysis and the confirmed catalytic activity of the observed black precipitate reveal that Pd nanoparticles are formed during the reactions and are stabilized by the carboxylic-functionalized thiourea ligands.



中文翻译:

室温下可恢复的Pd催化的好氧铃木-Miyaura水溶液反应的水溶性硫脲配体的合理设计和合成

摘要

制备了八种含有羧基官能化硫脲配体的预催化剂,并在有氧的Suzuki-Miyaura水溶液反应中评估了它们的活性和可回收性。具有四个羧基官能团的庞大的单硫脲-Pd复合物在芳基溴化物与芳基硼酸的偶联反应中显示出最佳的活性和可回收性。该催化剂可以重复使用至少五次,而其催化活性没有任何显着降低。TEM分析和所观察到的黑色沉淀物的确证催化活性表明,Pd纳米颗粒在反应过程中形成,并被羧基官能化的硫脲配体稳定。

制备了八种含有羧基官能化硫脲配体的预催化剂,并在有氧的Suzuki-Miyaura水溶液反应中评估了它们的活性和可回收性。具有四个羧基官能团的庞大的单硫脲-Pd复合物在芳基溴化物与芳基硼酸的偶联反应中显示出最佳的活性和可回收性。该催化剂可以重复使用至少五次,而其催化活性没有任何显着降低。TEM分析和所观察到的黑色沉淀物的确证催化活性表明,Pd纳米颗粒在反应过程中形成,并被羧基官能化的硫脲配体稳定。

更新日期:2018-01-04
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