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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

Wei Chen *, Xiao-Yan Lu*, Bei-Hua Xu, Wei-guo Yu, Zi-niu Zhou, Ying Hu

*Zhejiang Pharmaceutical College, Ningbo, Zhejiang, 315100; Ningbo No. 2 Hospital, Ningbo, Zhejiang, 315010, P. R. of China, Email: david_7788sina.com, xiao_yan_lu163.com

W. Chen, X.-Y. Lu, B.-Hua, W.-g. Yu, Z.-n. Zhou, Y. Hu, Synthesis, 2018, 50, 1499-1510.

DOI: 10.1055/s-0036-1589150 (free Supporting Information)


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Abstract

A bulky monothiourea-Pd complex shows a high activity and recyclability in aerobic aqueous Suzuki-Miyaura reactions of aryl bromides with arylboronic acids. The catalyst can be reused at least five times without any significant loss of catalytic activity. TEM analysis and the catalytic activity of the observed black precipitate reveal that Pd nanoparticles are formed and are stabilized by the carboxylic-functionalized thiourea ligands.

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Key Words

water-soluble, thiourea, ligands, palladium-catalyzed, Suzuki coupling, green chemistry


ID: J66-Y2018