Montmorillonite-Supported Copper(I) for Catalyzing N-Arylation of Nitrogen Heterocycles

doi:10.1016/S1872-2067(11)60458-0

Abstract

Abstract: Montmorillonite-supported copper (I) catalyst has been prepared by a simple ion exchange method. The resulting catalyst was characterized by X-ray diffraction, X-ray photoelectron spectroscopy, scanning electron microscopy, and energy dispersive X-ray spectrometry, with results showing that Cu⁺ had been successfully intercalated into the interlayer of Montmorillonite. The catalyst showed high levels of activity towards the N-arylation of nitrogen heterocycles with aryl chlorides or bromides. Furthermore, the catalyst could be reused up to four times without any significant loss in activity.

Key words: copper, montmorillonite, N-arylation reaction, aryl halides, heterogeneous catalyst

QI Xiao-Long, ZHOU Li-Mei, JIANG Xiao-Hui, FAN Hong-Wei, FU Hai-Yan, CHEN Hua. Montmorillonite-Supported Copper(I) for Catalyzing N-Arylation of Nitrogen Heterocycles[J]. Chinese Journal of Catalysis, 2012, 33(12): 1877-1882.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(11)60458-0

https://www.cjcatal.com/EN/Y2012/V33/I12/1877

References

1 Kison C, Opatz T. Chem Eur J, 2009, 15: 843
2 Kantam M L, Yadav J, Laha S, Sreedhar B, Jha S. Adv Synth Catal, 2007, 349: 1938
3 Evano G, Blanchard N, Toumi M. Chem Rev, 2008, 108: 3054
4 Monnier F, Taillefer M. Angew Chem, Int Ed, 2008, 47: 3096
5 Ma D, Cai Q. Acc Chem Res, 2008, 41: 1450
6 Lindley J. Tetrahedron, 1984, 40: 1433
7 Kunz K, Scholz U, Ganzer D. Synlett, 2003: 2428
8 Klapars A, Antilla J C, Huang X, Buchwald S L. J Am Chem Soc, 2001, 123: 7727
9 Zhu L, Li G, Luo L, Guo P, Lan J, You J. J Org Chem, 2007, 74: 2200
10 Xi Z, Liu F, Zhou Y, Chen W. Tetrahedron, 2008, 64: 4254
11 Choudary B M, Sridhar C, Kantam M L, Venkanna G T, Sreedhar B. J Am Chem Soc, 2005, 127: 9948
12 Likhar P R, Roy S, Roy M, Kantam M L, De R L. J Mol Catal A, 2007, 271: 57
13 Sreedhar B, Arundhathi R, Reddy P L, Reddy M A, Kantam M L. Synthesis, 2009, 15: 2517
14 Kantam M L, Rao B P C, Choudary B M, Reddy R S. Synlett, 2006: 2195
15 Reddy K R, Kumar N S, Sreedhar B, Kantam M L. J Mol Catal A, 2006, 252: 136
16 Amal Joseph P J, Priyadarshini S, Lakshmi Kantam M, Maheswaran H. Catal Sci Technol, 2011, 1: 234
17 Kantam M L, Roy M, Roy S, Bojja S, Lal De R. Catal Com-mun, 2008, 9: 2226
18 Arundhathi R, Kumar D C, Sreedhar B. Eur J Org Chem, 2010: 3621
19 Islam S M, Mondal S, Mondal P, Roy A S, Tuhina K, Salam N, Mobarak M. J Organomet Chem, 2012, 696: 4264
20 Mitsudome T, Nose K, Mori K, Mizugaki T, Ebitani K, Jitsu-kawa K, Kaneda K. Angew Chem, Int Ed, 2007, 46: 3228
21 Borah B J, Dutta D, Saikia P P, Barua N C, Dutta D K. Green Chem, 2011, 13: 3453
22 Holesova S, Kulhankova L, Martynkova G S, Kukutschova J, Capkova P. J Mol Struct, 2009, 923: 85
23 Shuai M, Liao L, Lu H B, Zhang L, Li J C, Fu D J. J Phys D, 2008, 41: 135010/1
24 Son S U, Park I K, Park J, Hyeon T. Chem Commun, 2004: 778
25 Huang Z, Li F, Chen B, Xue F, Chen G, Yuan G. Appl Catal A, 2011, 403: 104

[1]	Hui Gao, Gong Zhang, Dongfang Cheng, Yongtao Wang, Jing Zhao, Xiaozhi Li, Xiaowei Du, Zhi-Jian Zhao, Tuo Wang, Peng Zhang, Jinlong Gong. Steering electrochemical carbon dioxide reduction to alcohol production on Cu step sites [J]. Chinese Journal of Catalysis, 2023, 52(9): 187-195.
[2]	Na Zhou, Jiazhi Wang, Ning Zhang, Zhi Wang, Hengguo Wang, Gang Huang, Di Bao, Haixia Zhong, Xinbo Zhang. Defect-rich Cu@CuTCNQ composites for enhanced electrocatalytic nitrate reduction to ammonia [J]. Chinese Journal of Catalysis, 2023, 50(7): 324-333.
[3]	Yuzhuo Chen, Hao Wang, Bing Lu, Ni Yi, Liang Cao, Yong Wang, Shanjun Mao. Fine-structure sensitive deep learning framework for predicting catalytic properties with high precision [J]. Chinese Journal of Catalysis, 2023, 50(7): 284-296.
[4]	Zizi Li, Jia-Wei Wang, Yanjun Huang, Gangfeng Ouyang. Enhancing CO₂ photoreduction via the perfluorination of Co(II) phthalocyanine catalysts in a noble-metal-free system [J]. Chinese Journal of Catalysis, 2023, 49(6): 160-167.
[5]	Xianquan Li, Jifeng Pang, Yujia Zhao, Pengfei Wu, Wenguang Yu, Peifang Yan, Yang Su, Mingyuan Zheng. Ethanol dehydrogenation to acetaldehyde over a Cu^δ⁺-based Cu-MFI catalyst [J]. Chinese Journal of Catalysis, 2023, 49(6): 91-101.
[6]	Hangjie Li, Yuehua Xiao, Jiale Xiao, Kai Fan, Bingkuan Li, Xiaolong Li, Liang Wang, Feng-Shou Xiao. Selective hydrogenation of CO₂ into dimethyl ether over hydrophobic and gallium-modified copper catalysts [J]. Chinese Journal of Catalysis, 2023, 54(11): 178-187.
[7]	Huan Xue, Jia-Run Huang, Zhi-Shuo Wang, Zhen-Hua Zhao, Wen Shi, Pei-Qin Liao, Xiao-Ming Chen. Tailoring ligand fields of metal-azolate frameworks for highly selective electroreduction of CO₂ to hydrocarbons at industrial current density [J]. Chinese Journal of Catalysis, 2023, 53(10): 102-108.
[8]	Wanjun Sun, Jiayu Zhu, Meiyu Zhang, Xiangyu Meng, Mengxue Chen, Yu Feng, Xinlong Chen, Yong Ding. Recent advances and perspectives in cobalt-based heterogeneous catalysts for photocatalytic water splitting, CO₂ reduction, and N₂ fixation [J]. Chinese Journal of Catalysis, 2022, 43(9): 2273-2300.
[9]	Xuefei Weng, Shuangli Yang, Ding Ding, Mingshu Chen, Huilin Wan. Applications of in-situ wide spectral range infrared absorption spectroscopy for CO oxidation over Pd/SiO₂ and Cu/SiO₂ catalysts [J]. Chinese Journal of Catalysis, 2022, 43(8): 2001-2009.
[10]	Ya-Fei Jiang, Jin-Cheng Liu, Cong-Qiao Xu, Jun Li, Hai Xiao. Breaking the scaling relations for efficient N₂-to-NH₃ conversion by a bowl active site design: Insight from LaRuSi and isostructural electrides [J]. Chinese Journal of Catalysis, 2022, 43(8): 2183-2192.
[11]	Linlin Wang, Xin Li, Leiduan Hao, Song Hong, Alex W. Robertson, Zhenyu Sun. Integration of ultrafine CuO nanoparticles with two-dimensional MOFs for enhanced electrochemical CO₂ reduction to ethylene [J]. Chinese Journal of Catalysis, 2022, 43(4): 1049-1057.
[12]	Shi-Qun Cheng, Xue-Fei Weng, Qing-Nan Wang, Bai-Chuan Zhou, Wen-Cui Li, Ming-Run Li, Lei He, Dong-Qi Wang, An-Hui Lu. Defect-rich BN-supported Cu with superior dispersion for ethanol conversion to aldehyde and hydrogen [J]. Chinese Journal of Catalysis, 2022, 43(4): 1092-1100.
[13]	Yeqin Feng, Lin Qin, Junhao Zhang, Fangyu Fu, Huijie Li, Hua Xiang, Hongjin Lv. Wheel-shaped icosanuclear Cu-containing polyoxometalate catalyst: Mechanistic and stability studies on light-driven hydrogen generation [J]. Chinese Journal of Catalysis, 2022, 43(2): 442-450.
[14]	Jun Gong, Jinmeng Li, Chang Liu, Fengyuan Wei, Jinlong Yin, Wenzheng Li, Li Xiao, Gongwei Wang, Juntao Lu, Lin Zhuang. Guanine-regulated proton transfer enhances CO₂-to-CH₄ selectivity over copper electrode [J]. Chinese Journal of Catalysis, 2022, 43(12): 3101-3106.
[15]	Li Zhu, Yiyang Lin, Kang Liu, Emiliano Cortés, Hongmei Li, Junhua Hu, Akira Yamaguchi, Xiaoliang Liu, Masahiro Miyauchi, Junwei Fu, Min Liu. Tuning the intermediate reaction barriers by a CuPd catalyst to improve the selectivity of CO₂ electroreduction to C2 products [J]. Chinese Journal of Catalysis, 2021, 42(9): 1500-1508.