Synthesis and Catalytic Characteristics of a Silica-Supported Poly-ω-(methylseleno)undecylsiloxane Palladium(0) Complex

Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (02): 215-218. Previous Articles Next Articles

Original Articles

聚-ω-(甲硒基)十一烷基硅氧烷钯(0)配合物的合成与催化性能

刘刚¹,2，章荣立¹，*^,1

(¹江西师范大学化学化工学院南昌 330027)
(²江西科技师范学院化学系南昌 330013)

收稿日期:2005-03-24 修回日期:2005-08-26 发布日期:2006-01-21
通讯作者: 蔡明中

Synthesis and Catalytic Characteristics of a Silica-Supported Poly-ω-(methylseleno)undecylsiloxane Palladium(0) Complex

LIU Gang¹,2,ZHANG Rong-Li¹,CAI Ming-Zhong*^,1

(¹School of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330027)
(²Department of Chemistry, Jiangxi Teaching College of Science and Tech-nology, Nanchang 330013)

Received:2005-03-24 Revised:2005-08-26 Published:2006-01-21
Contact: CAI Ming-Zhong

Abstract

A simple and practical synthetic method for the cinnamonitriles and cinnamic acids was presented. A silica-supported poly-ω-(methylseleno)undecylsiloxane palladium(0) complex has been prepared from ω-chloroundecyltriethoxysilane via immobilization on fumed silica, followed by reaction with sodium methylselenolate in ethanol and palladium chloride in acetone, and then reduction with hydrazine hydrate in ethanol. The title complex was a highly active and stereoselective catalyst for arylation of acry-lonitrile and acrylic acid with aryl iodides, and could be recovered and reused.

Key words: Heck arylation, cinnamic acid, cinnamonitrile, stereoselective synthesis, selenide palladium(0) complex, supported palladium catalyst

Cite this article

LIU Gang^1,2,ZHANG Rong-Li,CAI Ming-Zhong*^,1. Synthesis and Catalytic Characteristics of a Silica-Supported Poly-ω-(methylseleno)undecylsiloxane Palladium(0) Complex[J]. Chin. J. Org. Chem., 2006, 26(02): 215-218.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Yangxing Sun, Yanzhi Li, Yanlai Cao, Nengzhong Wang, Shaohua Xiang, Mingguo Liu, Hui Yao. Research Advances in Functional Group-Directed Stereoselective Glycosylation [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3506-3529.
[2]	Lin Zhiqing, Xia Wanling, Liu Renyi, Jiang Shaohua, Ma Zhiqiang. Synthesis of Cinnamic Acid-Coumarin Ester Analogs and Inhibition of Tyrosinase Activity [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2980-2987.
[3]	Acid Wang Weiwei, Zhao Yu, Liu Xinlei, Geng Rui, Wang Mingan. Synthesis of (E)-3-Aryl-7-methylocta-2,6-dienoic Acid via Stereoselective Mizoroki-Heck Arylation of (E)-7-Methylocta-2,6-dienoic [J]. Chin. J. Org. Chem., 2019, 39(4): 1129-1135.
[4]	Liao Fumin, Yu Jinsheng, Zhou Jian. Recent Advances in the Highly Stereoselective Synthesis of Tri-or Tetra-substituted Monofluoroalkenes [J]. Chin. J. Org. Chem., 2017, 37(9): 2175-2186.
[5]	Gao Yanjiao, Xiao Zhenhua, Liu Liangxian, Huang Peiqiang. Direct Reductive Cyanation of A 2-Pyrrolidinone Chiral Building Block Bearing An Unprotected Hydroxyl Group: A Stereoselective Synthesis of N-Methyl-2-epi-bulgecinine [J]. Chin. J. Org. Chem., 2017, 37(5): 1189-1197.
[6]	Hei Liying, Feng Cuilan, Li Zhen, Liu Lantao, Gui Jianzhou. Microporous Network Polyaniline Coated Magnetic Fe₃O₄ Nanoparticals Supported Palladium Catalyzed Suzuki and Heck Coupling Reactions [J]. Chin. J. Org. Chem., 2015, 35(8): 1673-1681.
[7]	Yuan Dingzhong, Huang Bin. Progress in Organic Synthesis Reactions Catalyzed by Palladium Supported on Magnetic Nanoparticles [J]. Chin. J. Org. Chem., 2012, 32(08): 1368-1379.
[8]	Yang Zhen, Jing Peng, She Xuegong. A Stereoselective Synthesis of the C(13)-C(23) Fragment of Iriomoteolide-1b [J]. Chin. J. Org. Chem., 2012, 32(02): 338-343 .
[9]	YANG Shu-Xin, CHEN Jie, WU Xiao-Yu, DENG Hong-Mei, SHAO Min, ZHANG Hui, CAO Wei-Guo. Facile, Highly Stereoselective Synthesis of Spiro[cyclopropane-1,3 - indolin]-2 -ones and Spiro[cyclopropane-1,2 -indane]-1 ,3 -diones Containing Trifluoromethyl Group [J]. Chin. J. Org. Chem., 2010, 30(10): 1521-1528.
[10]	XU Xiao-Bo, YANG Ying-Bin, DENG Qin, XIANG Li, XIANG Jian-Nan. Stereoselective Synthesis of 4-Acetoxyazetidione: the Key Intermediate of Penem and Carbapenem Antibiotics [J]. Chin. J. Org. Chem., 2010, 30(07): 1017-1020.
[11]	YAN Mei, FENG Xiu-Juan. >Advances in Suzuki Coupling Reactions Catalyzed by Supported Palladium Catalysts [J]. Chin. J. Org. Chem., 2010, 30(05): 623-632.
[12]	WANG Meng, ZHANG Hui, CHEN Jie, TUN Xiao-Tu, DENG Gong-Mei. Highly Stereoselective Synthesis of Spiro[cyclopropane-1,4'- pyrazolin-5'-one] Derivertives via Ammonium Ylide [J]. Chin. J. Org. Chem., 2009, 29(10): 1611-1616.
[13]	Duan, Huaxin^a ; Zhang, Shujia^*,a,b ; Zhou, Peng^a. Synthesis and Antitumor Activity of 20(S)-O-Linked Camptothecin Cinnamic Acid Ester Derivatives [J]. Chin. J. Org. Chem., 2009, 29(05): 724-729.
[14]	YU La-Mei^a,XU Qiu-Hua^b,CAI Ming-Zhong*^,a. Synthesis of MCM-41-Supported Thioether Palladium Complex and Its Catalytic Properties in Carbonylation of Aryl Halides [J]. Chin. J. Org. Chem., 2008, 28(2): 256-260.
[15]	GENG, Xiao-Hong; ZHOU, Hui; CHEN, Pei-Ran* ; XU, Qing. Recent Advances in the Stereoselective Synthesis of α-Cyanohydrins [J]. Chin. J. Org. Chem., 2008, 28(07): 1157-1163.

聚-ω-(甲硒基)十一烷基硅氧烷钯(0)配合物的合成与催化性能

Synthesis and Catalytic Characteristics of a Silica-Supported Poly-ω-(methylseleno)undecylsiloxane Palladium(0) Complex

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments