Synthesis 2018; 50(07): 1499-1510
DOI: 10.1055/s-0036-1589150
paper
© Georg Thieme Verlag Stuttgart · New York

The Rational Design and Synthesis of Water-Soluble Thiourea Ligands for Recoverable Pd-Catalyzed Aerobic Aqueous Suzuki–Miyaura Reactions at Room Temperature

a  Department of Pharmaceutical Engineering, Zhejiang Pharmaceutical College, 888 Yinxian Avenue Eastern Section, Ningbo, Zhejiang, 315100, P. R. of China   Email: david_7788@sina.com
,
Xiao-Yan Lu*
b  Department of Pharmacy, Ningbo No. 2 Hospital, 41 Northwest Street, Ningbo, Zhejiang, 315010, P. R. of China   Email: xiao_yan_lu@163.com
,
Bei-Hua Xu
a  Department of Pharmaceutical Engineering, Zhejiang Pharmaceutical College, 888 Yinxian Avenue Eastern Section, Ningbo, Zhejiang, 315100, P. R. of China   Email: david_7788@sina.com
,
Wei-guo Yu
a  Department of Pharmaceutical Engineering, Zhejiang Pharmaceutical College, 888 Yinxian Avenue Eastern Section, Ningbo, Zhejiang, 315100, P. R. of China   Email: david_7788@sina.com
,
Zi-niu Zhou
a  Department of Pharmaceutical Engineering, Zhejiang Pharmaceutical College, 888 Yinxian Avenue Eastern Section, Ningbo, Zhejiang, 315100, P. R. of China   Email: david_7788@sina.com
,
Ying Hu
a  Department of Pharmaceutical Engineering, Zhejiang Pharmaceutical College, 888 Yinxian Avenue Eastern Section, Ningbo, Zhejiang, 315100, P. R. of China   Email: david_7788@sina.com
› Author Affiliations
We are grateful for the financial support from the National Natural Science Foundation of China (21502172), Zhejiang Provincial Natural Science Foundation of China (LQ13B020005, LQ15H300001), the Science and Technology Innovation Team Project of Ningbo Science and Technology Bureau, China (2015C110027), the Key Laboratory of Ningbo, China (2016A22002) and the Ningbo Natural Science Foundation (2015A610284).
Further Information

Publication History

Received: 31 August 2017

Accepted after revision: 14 October 2017

Publication Date:
04 January 2018 (online)


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.

Supporting Information

 
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