Citation: Chen Qiang, Fan Xinheng, Zhang Lipeng, Yang Lianming. A Simple Nickel(Ⅱ) Catalyst System for the Addition of Arylboronic Acids to Arylaldehydes[J]. Chemistry, ;2018, 81(12): 1115-1120. shu

A Simple Nickel(Ⅱ) Catalyst System for the Addition of Arylboronic Acids to Arylaldehydes

Chen Qiang ^1,2 ,
Fan Xinheng ^1,, ,
Zhang Lipeng ^1,2 ,
Yang Lianming ^1,,

1.
Beijing National Laboratory for Molecular Sciences(BNLMS), Key Laboratory of Green Printing, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190
2.
University of Chinese Academy of Sciences, Beijing 100049

Corresponding author: Fan Xinheng, xinxin9968@iccas.ac.cn Yang Lianming, yanglm@iccas.ac.cn
Received Date: 10 July 2018
Accepted Date: 30 August 2018

A facile procedure for the catalytic addition of arylboronic acids to aromatic aldehydes was developed using a simple NiCl₂(PPh₃)₂/IPr·HCl system under mild conditions, providing diarylmethanols in high yields. This method is simple and easy to handle, which is an important supplement to the preparation of diaryl methanols.
- Nickel(Ⅱ),
- Catalytic reaction,
- Diaryl methanol
1. [1]
  S Mondal, G Panda. RSC Adv., 2014, 4(54):28317~28358, and references cited therein.
2. [2]
  M Seto, Y Aramaki, H Imoto et al. Chem. Pharm. Bull., 2004, 52(7):818~829, and references cited therein.
3. [3]
  M Sakai, M Ueda, N Miyaura. Angew. Chem. Int. Ed., 1998, 37(23):3279~3281.
4. [4]
  Selected examples of Rh catalyst:(a) M Ueda, N Miyaura. J. Org. Chem., 2000, 65(14):4450~4452; (b) A F Trindade, P M P Gois, L F Veiros et al. J. Org. Chem., 2008, 73(11):4076~4086; (c) J R White, G J Price, P K Plucinski et al. Tetrahed. Lett., 2009, 50(52):7365~7368; (d) C H Xing, T P Liu, J R Zheng et al. Tetrahed. Lett., 2009, 50(35):4953~4957; (e) A F Trindade, V André, M T Duarte et al. Tetrahedron, 2010, 66(44):8494~8502; (f) S Denizalti, H Türkmen, B Cetinkaya, Tetrahed. Lett., 2014, 55(30):4129~4132; (g) J Yang, X Chen, Z Wang, Tetrahed. Lett., 2015, 56(41):5673~5675; (h) L S Dobson, G Pattison. Chem. Commun., 2016, 52(74):11116~11119; (i) M Veguillas, J Rojas-Martín, M Ribagorda et al. Org. Biomol. Chem., 2017, 15(25):5386~5394.
5. [5]
  Selected examples of Pd catalyst:(a) T Yamamoto, T Ohta, Y Ito. Org. Lett., 2005, 7(19):4153~4155; (b) K Suzuki, T Arao, S Ishii et al. Tetrahed. Lett., 2006, 47(32):5789~5792; (c) C Qin, H Wu, J Cheng et al. J. Org. Chem., 2007, 72(11):4102~4107; (d) P He, Y Lu, C G Dong et al. Org. Lett., 2007, 9(2):343~346; (e) P He, Y Lu, Q S Hu, Tetrahed. Lett., 2007, 48(30):5283~5288; (f) M Kuriyama, R Shimazawa, T Enomoto et al. J. Org. Chem., 2008, 73(17):6939~6942; (g) A Yu, B Cheng, Y Wu et al. Tetrahed. Lett., 2008, 49(37):5405~5407; (h) M Kuriyama, N Ishiyama, R Shimazawa et al. Tetrahedron, 2010, 66(34):6814~6819; (i) T Yamamoto, T Furusawa, A Zhumagazin et al. Tetrahedron, 2015, 71(1):19~26; (j) W He, B Zhou, Y Zhou et al. Tetrahed. Lett., 2016, 57(29):3152~3155.
6. [6]
  Y X Liao, C H Xing, P He et al. Org. Lett., 2008, 10(12):2509~2512.
7. [7]
  (a) Y Yamamoto, K Kurihara, N Miyaura. Angew. Chem. Int. Ed., 2009, 48(24):4414~4416; (b) K Li, N Hu, R Luo et al. J. Org. Chem., 2013, 78(12):6350~6355.
8. [8]
  Selected examples of Ni catalyst:(a) G Takahashi, E Shirakawa, T Tsuchimoto et al. Chem. Commun., 2005, (11):1459~1461; (b) T Arao, K Kondo, T Aoyama. Tetrahed. Lett., 2007, 48(23):4115~4117; (c) J Bouffard, K Itami. Org. Lett., 2009, 11(19):4410~4413; (d) C H Xing, Q S Hu, Tetrahed. Lett., 2010, 51(6):924~927; (e) W Chen, M Baghbanzadeh, C O Kappe. Tetrahed. Lett., 2011, 52(14):1677~1679.
9. [9]
  L Zhou, X Du, R He et al. Tetrahed. Lett., 2009, 50(4):406~408.
1. [1]
  Weiping Xiao , Yuhang Chen , Qin Zhao , Danil Bukhvalov , Caiqin Wang , Xiaofei Yang . Constructing the synergistic active sites of nickel bicarbonate supported Pt hierarchical nanostructure for efficient hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(12): 110176-. doi: 10.1016/j.cclet.2024.110176
2. [2]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
3. [3]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068
4. [4]
  Fenglin Wang , Chengwei Kuang , Zhicheng Zheng , Dan Wu , Hao Wan , Gen Chen , Ning Zhang , Xiaohe Liu , Renzhi Ma . Noble metal clusters substitution in porous Ni substrate renders high mass-specific activities toward oxygen evolution reaction and methanol oxidation reaction. Chinese Chemical Letters, 2025, 36(6): 109989-. doi: 10.1016/j.cclet.2024.109989
5. [5]
  Zhenkang Ai , Hui Chen , Xuebin Liao . Nickel-catalyzed decarboxylative difluoromethylation and alkylation of alkenes. Chinese Chemical Letters, 2025, 36(3): 109954-. doi: 10.1016/j.cclet.2024.109954
6. [6]
  Xiao-Bo Liu , Ren-Ming Liu , Xiao-Di Bao , Hua-Jian Xu , Qi Zhang , Yu-Feng Liang . Nickel-catalyzed reductive formylation of aryl halides via formyl radical. Chinese Chemical Letters, 2024, 35(12): 109783-. doi: 10.1016/j.cclet.2024.109783
7. [7]
  Yu-Hang Miao , Zheng-Xu Zhang , Xu-Yi Huang , Yuan-Zhao Hua , Shi-Kun Jia , Xiao Xiao , Min-Can Wang , Li-Ping Xu , Guang-Jian Mei . Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles. Chinese Chemical Letters, 2024, 35(4): 108830-. doi: 10.1016/j.cclet.2023.108830
8. [8]
  Fangqing Zhang , Yu Wang , Zhenda Tan , Yangbin Liu , Lijuan Song , Xiaoming Feng . Catalytic asymmetric inverse-electron-demand Diels–Alder reaction of 2-pyrones with aryl enol ethers. Chinese Chemical Letters, 2025, 36(7): 110581-. doi: 10.1016/j.cclet.2024.110581
9. [9]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO₂ cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415
10. [10]
  Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
11. [11]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
12. [12]
  Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
13. [13]
  Qiang Wu , Baofeng Wang . Exploring synthetic strategy for stabilizing nickel-rich layered oxide cathodes through structural design. Chinese Chemical Letters, 2024, 35(12): 110089-. doi: 10.1016/j.cclet.2024.110089
14. [14]
  Jumei Zhang , Ziheng Zhang , Gang Li , Hongjin Qiao , Hua Xie , Ling Jiang . Ligand-mediated reactivity in CO oxidation of yttrium-nickel monoxide carbonyl complexes. Chinese Chemical Letters, 2025, 36(2): 110278-. doi: 10.1016/j.cclet.2024.110278
15. [15]
  Shaobin He , Xiaoyun Guo , Qionghua Zheng , Huanran Shen , Yuan Xu , Fenglin Lin , Jincheng Chen , Haohua Deng , Yiming Zeng , Wei Chen . Engineering nickel-supported osmium bimetallic nanozymes with specifically improved peroxidase-like activity for immunoassay. Chinese Chemical Letters, 2025, 36(4): 110096-. doi: 10.1016/j.cclet.2024.110096
16. [16]
  Fan Chen , Xiaoyu Zhao , Weihang Miao , Yingying Li , Ye Yuan , Lingling Chu . Regio- and enantioselective hydrofluorination of internal alkenes via nickel-catalyzed hydrogen atom transfer. Chinese Chemical Letters, 2025, 36(5): 110239-. doi: 10.1016/j.cclet.2024.110239
17. [17]
  Hui Yang , Guangxun Zhang , Yueyao Sun , Huijie Zhou , Huan Pang . Bimetallic zeolitic imidazolate framework derived hollow layered double hydroxide with tailorable interlayer spacing for nickel-zinc batteries. Chinese Chemical Letters, 2025, 36(6): 110016-. doi: 10.1016/j.cclet.2024.110016
18. [18]
  Xianzheng Zhang , Yana Chen , Zhiyong Ye , Huilin Hu , Ling Lei , Feng You , Junlong Yao , Huan Yang , Xueliang Jiang . Magnetic field-assisted microbial corrosion construction iron sulfides incorporated nickel-iron hydroxide towards efficient oxygen evolution. Chinese Journal of Structural Chemistry, 2024, 43(1): 100200-100200. doi: 10.1016/j.cjsc.2023.100200
19. [19]
  Chunru Liu , Ligang Feng . Advances in anode catalysts of methanol-assisted water-splitting reactions for hydrogen generation. Chinese Journal of Structural Chemistry, 2023, 42(10): 100136-100136. doi: 10.1016/j.cjsc.2023.100136
20. [20]
  Xinyi Hu , Riguang Zhang , Zhao Jiang . Depositing the PtNi nanoparticles on niobium oxide to enhance the activity and CO-tolerance for alkaline methanol electrooxidation. Chinese Journal of Structural Chemistry, 2023, 42(11): 100157-100157. doi: 10.1016/j.cjsc.2023.100157

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(298)
HTML views(35)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142