Li2 PdCI4-CuCI catalyzed reactions of arenediazonium salts with methyl acrylic acid

Abstract

With Li2PdCl4-CuCl as catalyst, arenediazonium fluoroborates RC6H4N2BF4 (R = H, p-CH3, p-CH3O, o-Cl, m-Cl, p-Cl, o-NO2, m-NO2, o-COOH, m-CO2H, p-CO2H) reacted with Me acrylate in methanol to give (E)-RC6H4CH:CHCO2Me in 78-98% yields. Similar yields of arylation products were obtained when Me acrylate was replaced by acrylic acid.

Key words: DIAZO COMPOUNDS, CATALYST, CHLORIDE, ACRYLIC ACID, CHLORO COMPLEX, LITHIUM COMPOUNDS, COPPER COMPOUNDS, ARYL GROUP, PALLADIUM CHLORIDE, PROPENOIC ACID ESTER, FLUOROBORATE, PALLADATE P

CLC Number:

O627

Cite this article

XU JIANHUA;TAN LUSHI;HU HONGWEN. Li2 PdCI4-CuCI catalyzed reactions of arenediazonium salts with methyl acrylic acid[J]. Chin. J. Org. Chem., 1987, 7(6): 452-454.

[1]	Gangzhong Jiang, Jiaxing Lin, Xiaoguang Bao, Xiaobing Wan. Isoamyl Nitrite Activated Primary Sulfonamide to Sulfonyl Bromide and Sulfonyl Chloride [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 533-549.
[2]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[3]	Jianghu Dong, Liangming Xuan, Chi Wang, Chenxi Zhao, Haifeng Wang, Qiongjiao Yan, Wei Wang, Fen'er Chen. Recent Advances in Visible-Light-Induced C(3)—H Functionalization of Quinoxalinones under Transition-Metal-Free or Photocatalyst-Free [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 111-136.
[4]	Xiaoping Xu, Yifei Zhang, Xiaoyu Mo, Jun Jiang. Rh-Catalyzed C—H Functionalization Reaction between 3-Diazoindolin-2-imines and Pyrazolones for the Construction of 3-Pyrazolyl Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2519-2527.
[5]	Kai Lu, Haoqi Qu, Xi Chen, Hui Qiu, Jing Zheng, Mengtao Ma. Catalyst-Free and Solvent-Free Hydroboration of Alkynes and Alkenes with Catecholborane [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2197-2205.
[6]	Xiaoyu Lu, Xiaomei Sun, Yaqing Niu, Junchao Wang, Wenjing Yin, Mengting Gao, Zi Liu, Zhenghuan Wei, Tinghua Tao. Copper-Catalyzed Decarboxylative Cross-Coupling of α‑Fluoroacrylic Acids with N-Tosyl Oxaziridines [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2110-2119.
[7]	Weina Tian, Liang Xu, Yu Wei, Pengfei Li. Synthesis of Isoquinoline-3-carboxylate Chelated B,B-Diaryl Tetracoordinated Organoboron Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1792-1798.
[8]	Zhicheng Bao, Muyao Li, Jianbo Wang. Copper-Catalyzed Cross-Coupling of Aryldiazoacetates with Bis[(pinacolato)boryl]methane [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1808-1814.
[9]	Baichuan Mo, Chunxia Chen, Jinsong Peng. Research Progress in Application of Lignin and Its Derivatives Supported Metal Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1215-1240.
[10]	Sining Qin. Research Progress in C—S Coupling Reactions of Aryl Halides [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3761-3783.
[11]	Tiantian Liu, Xinhong Duan. Recent Progress in the Construction of Chiral 3-Substituted Indoles by Asymmetric Friedel-Crafts Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3695-3712.
[12]	Zhiyuan Chen, Mengwei Yang, Jianlin Xu, Yunhe Xu. Regioselective Synthesis of β-Silyl-Substituted Vinylphosphine Oxides via Copper-Catalyzed Protosilylation of Dialkynylphosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3598-3607.
[13]	Xiangkun Meng, Zhengyuan Qi, Lei Yu, Yiyang Zhang. Catalytic System for Poly(lactic acid) Synthesis: Opportunities and Challenges [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 112-119.
[14]	Xudong Cui, Xiangkun Meng, Ying Chen, Yonghong Liu, Lei Yu. Preparation of L-Lactide with High Optical Purity via the Zinc-Doped Polypyrrole-Catalyzed Lactic Acid Condensation [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2954-2960.
[15]	Shouyi Cen, Zhipeng Zhang. Synthesis of Biphenanthrol-Based Confined Chiral Phosphoric Acid [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2574-2581.

Li2PdCl4-CuCl催化的芳基重氮氟硼酸盐与丙烯酸及其甲酯的反应