Aryl-guanidine/Pd-catalyzed Suzuki Cross-coupling Reaction at Room Temperature

高等学校化学研究 ›› 2012, Vol. 28 ›› Issue (2): 242-244 .

Aryl-guanidine/Pd-catalyzed Suzuki Cross-coupling Reaction at Room Temperature

LI Yan-chun¹, LIN Ying-jie¹, ZHANG Suo-bo², LI Sheng-hai², DUAN Hai-feng¹

1. Departent of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130012, P. R. China;
2. Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China

收稿日期:2011-04-18 修回日期:2011-07-22 出版日期:2012-03-25 发布日期:2012-03-08
通讯作者: LI Sheng-hai, DUAN Hai-feng E-mail:lsh@ciac.jl.cn; duanhf@jlu.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(Nos.20802071, 21074133).

Aryl-guanidine/Pd-catalyzed Suzuki Cross-coupling Reaction at Room Temperature

LI Yan-chun¹, LIN Ying-jie¹, ZHANG Suo-bo², LI Sheng-hai², DUAN Hai-feng¹

1. Departent of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130012, P. R. China;
2. Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China

Received:2011-04-18 Revised:2011-07-22 Online:2012-03-25 Published:2012-03-08
Supported by:
Supported by the National Natural Science Foundation of China(Nos.20802071, 21074133).

摘要/Abstract

摘要： Four aryl-guanidines(AG) were synthesized and used for the palladium-catalyzed Suzuki cross-coupling reaction to test the catalytic activity. In the presence of steric bulk AG, when aryl bromide and arylboronic acid were used as the reactants, the Suzuki reaction could be carried out smoothly at room temperature in aqueous solvent to afford the cross-coupling product in high yield. This catalysis system was also successful for the coupling of activated aryl chlorides at room temperature.

关键词: Aryl-guanidine, Suzuki reaction, Palladium, Ligand

Abstract: Four aryl-guanidines(AG) were synthesized and used for the palladium-catalyzed Suzuki cross-coupling reaction to test the catalytic activity. In the presence of steric bulk AG, when aryl bromide and arylboronic acid were used as the reactants, the Suzuki reaction could be carried out smoothly at room temperature in aqueous solvent to afford the cross-coupling product in high yield. This catalysis system was also successful for the coupling of activated aryl chlorides at room temperature.

Key words: Aryl-guanidine, Suzuki reaction, Palladium, Ligand

LI Yan-chun, LIN Ying-jie, ZHANG Suo-bo, LI Sheng-hai, DUAN Hai-feng. Aryl-guanidine/Pd-catalyzed Suzuki Cross-coupling Reaction at Room Temperature[J]. 高等学校化学研究, 2012, 28(2): 242-244 .

LI Yan-chun, LIN Ying-jie, ZHANG Suo-bo, LI Sheng-hai, DUAN Hai-feng. Aryl-guanidine/Pd-catalyzed Suzuki Cross-coupling Reaction at Room Temperature[J]. Chemical Research in Chinese Universities, 2012, 28(2): 242-244 .

[1]	HU Lingling, LIU Ke, REN Guolan, LIANG Jiangong, WU Yuan. Progress in DNA Aptamers as Recognition Components for Protein Functional Regulation[J]. 高等学校化学研究, 2022, 38(4): 894-901.
[2]	LAN Weifei, HU Ruifeng, HUANG Danrong, DONG Xu, SHEN Gangyi, CHANG Shan, DAI Dongsheng. Palladium Nanoparticles/Graphdiyne Oxide Nanocomposite with Excellent Peroxidase-like Activity and Its Application for Glutathione Detection[J]. 高等学校化学研究, 2022, 38(2): 529-534.
[3]	HUA Chen, YI Pin, LIU Wencong, WANG Mengfan, NIU Zheng, LANG Jianping. Coordination Polymers with Bipyridyl Diene and Triene Ligands: Synthesis, Structures and Luminescent Properties[J]. 高等学校化学研究, 2022, 38(1): 209-216.
[4]	CAI Yanchun, JIAO Long, QIU Xuepeng, DU Zhijun. Promotion Mechanism of H₂O for Stereoselectivity in Pd(II)-catalyzed C—H Arylation of Diarylphosphinamides with Arylboronic Acids[J]. 高等学校化学研究, 2020, 36(5): 843-846.
[5]	YU Wenting, XUE Bin, ZHU Zhenshu, SHEN Ziqin, QIN Meng, WANG Wei, CAO Yi. Strong and Injectable Hydrogels Based on Multivalent Metal Ion-Peptide Cross-linking[J]. 高等学校化学研究, 2020, 36(5): 962-969.
[6]	LI Ruyue, WU Mingwei, PAN Biwei, LI Meng, HUANG Jun. Aerobic Oxidation of Alcohols to Aldehydes and Ketones with Recyclable Pd Catalysts on Cross-linked 1,10-Phenanthroline Polymers[J]. 高等学校化学研究, 2020, 36(5): 934-939.
[7]	YU Wenli, ZHANG Mingjuan, LIU Kang, YANG Yu, WANG Lei. Hydrogen Bonding Assembled 3D Supramolecular Structures Formed by 5-Amino-2,4,6-triiodoisophthalic Acid and N-Heterocyclic Aromatic Ligands[J]. 高等学校化学研究, 2019, 35(5): 806-811.
[8]	CHEN Weimin, ZHANG Yu, ZHU Zhenyu. Effects of Cerium Oxides on the Catalytic Performance of Pd/CNT for Methanol Oxidation[J]. 高等学校化学研究, 2019, 35(1): 133-138.
[9]	WANG Yingnan, WEI Chiyu, SONG Zhiguang. Facile Synthesis of 1,5-Diaryl-4-pyridyl-1,2,3-triaozle Derivatives[J]. 高等学校化学研究, 2018, 34(6): 923-928.
[10]	CHEN Liduo, HUO Hongliang, WANG Libo, MA Lili, JIANG Yan, XIE Junyi, WANG Jun. Nickel Complexes Based on Salicylaldehyde-imine Ligands: Synthesis, Characterization and Catalytic Oligomerization of Ethylene[J]. 高等学校化学研究, 2018, 34(6): 945-951.
[11]	ZHOU Xiaojing, LIU Lili, TAI Xishi, ZHANG Hui. (3,3)-Connected Three-dimentional Supramolecular Metal Organic Polyhedral Based on Nanometresized Ligand with Magnetism Properties[J]. 高等学校化学研究, 2018, 34(5): 723-726.
[12]	REN Xiuqing, FU Xuemei, LIN Xinzhang, LIU Chao, HUANG Jiahui, YAN Jinghui. Highly Efficient Synthesis of Au₁₃₀(SPh-Br)₅₀ Nanocluster[J]. 高等学校化学研究, 2018, 34(5): 719-722.
[13]	WANG Shihui, LI Haiyan, WANG Yue, GAO Yang, YU Shanshan, ZHAO Qianqian, JIN Xiangqun, LU Haibin. Design and Synthesis of Proteolysis Targeting Chimeras for Inducing BRD4 Protein Degradation[J]. 高等学校化学研究, 2018, 34(2): 221-228.
[14]	LIU Chengxin, HAN Fangwai, LIU Guiyan, ZHAO Hongkun. Synthesis of (Ph₃P)₂PdX₂ Complexes and Their Catalytic Activity for Heck Reaction Involving Aryl Halide and Acrylate[J]. 高等学校化学研究, 2017, 33(6): 860-863.
[15]	LI Yanjie, ZHANG Xingmin, NIU Shengxiu, ZHAO Yanping, YANG Lijuan, SHAO Xiaowei, WANG Ensi. Synthesis and Biological Activity of Imidazo[4,5-c]quinoline Derivatives as PI3K/mTOR Inhibitors[J]. 高等学校化学研究, 2017, 33(6): 895-902.

Aryl-guanidine/Pd-catalyzed Suzuki Cross-coupling Reaction at Room Temperature

Aryl-guanidine/Pd-catalyzed Suzuki Cross-coupling Reaction at Room Temperature

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价