Citation: Yanli Cui, Xiaoning Guo, Yingyong Wang, Xiangyun Guo. Carbonylative Suzuki coupling reactions of aryl iodides with arylboronic acids over Pd/SiC[J]. Chinese Journal of Catalysis, ;2015, 36(3): 322-327. doi: 10.1016/S1872-2067(14)60258-8 shu

Carbonylative Suzuki coupling reactions of aryl iodides with arylboronic acids over Pd/SiC

1.
a State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, Shanxi, China;

Corresponding author: Xiaoning Guo,
Received Date: 14 September 2014
Available Online: 28 November 2014
Fund Project: 国家自然科学基金(21203233) (21203233) 山西省自然科学基金(2013021007-1). (2013021007-1)

High surface area SiC has been used to prepare a Pd/SiC catalyst using the liquid reduction method, and the resulting catalyst was used for the carbonylative Suzuki coupling reaction of aryl iodides with arylboronic acids. The catalyst was also characterized by X-ray diffraction, inductively coupled plasma-mass spectroscopy and high-resolution transmission electron microscopy. The results of these analyses showed that homogeneous Pd nanoparticles with a mean diameter of 2.8 nm were uniformly dispersed on the SiC surface. Optimization of the reaction conditions for the carbonylative Suzuki coupling reaction, including the solvent, base, pressure, temperature and reaction time, revealed that the model reaction of iodobenzene (1.0 mmol) with phenylboronic acid (1.5 mmol) could reach 90% conversion with a selectivity of 99% towards the diphenyl ketone using 3 wt% Pd/SiC under 1.0 MPa of CO pressure at 100 ℃ for 8 h with K₂CO₃ (3.0 mmol) as the base and anisole as the solvent. The Pd/SiC catalyst exhibited broad substrate scope towards the carbonylative Suzuki coupling reaction of aryl iodides with arylboronic acids bearing a variety of different substituents. Furthermore, the Pd/SiC catalyst exhibited good recyclability properties and could be recovered and reused up to five times with the conversion of iodobenzene decreasing only slightly from 90% to 76%. The decrease in the catalytic activity after five rounds was attributed to the loss of active Pd during the organic reaction.
- Palladium/silicon carbide,
- Carbonylation Suzuki coupling,
- Aryl iodide,
- Arylboronic acid,
- Heterogeneous catalysis
1. [1]
  [1] Wang X J, Zhang L, Sun X F, Xu Y B, Krishnamurthy D, Senanayake C H. Org Lett, 2005, 7: 5593
2. [2]
  [2] Hatano B, Kadokaw J, Tagaya H. Tetrahedron Lett, 2002, 43: 5859
3. [3]
  [3] Gmouh S, Yang H L, Vaultier M. Org Lett, 2003, 5: 2219
4. [4]
  [4] Yamamoto T, Kohara T, Yamamoto A. Chem Lett, 1976, 11: 1217
5. [5]
  [5] Hatanaka Y, Fukushima S, Hiyama T. Tetrahedron, 1992, 48: 2113
6. [6]
  [6] Brunet J J, Chauvin R. Chem Soc Rev, 1995, 24: 89
7. [7]
  [7] Fillion E, Fishlock D, Wilsily A, Goll J M. J Org Chem, 2005, 70: 1316
8. [8]
  [8] Jang D O, Moon K S, Cho D H, Kim J G. Tetrahedron Lett, 2006, 47: 6063
9. [9]
  [9] Ishiyama T, Kizaki H, Miyaura N, Suzuki A. Tetrahedron Lett, 1993, 34: 7595
10. [10]
  [10] Ishiyama T, Kizaki H, Hayashi T, Suzuki A, Miyaura N. J Org Chem, 1998, 63: 4726
11. [11]
  [11] Khedkar M V, Sasaki T, Bhanage B M. RSC Adv, 2013, 3: 7791
12. [12]
  [12] Niu J R, Liu M M, Wang P, Long Y, Xie M, Li R, Ma J T. New J Chem, 2014, 38: 1471
13. [13]
  [13] Zhan Y Y, Cai G H, Zheng Y, Shen X N, Zheng Y, Wei K M. Acta Phys- Chim Sin (詹瑛瑛, 蔡国辉, 郑勇, 沈小女, 郑瑛, 魏可镁. 物理化学学报), 2008, 24: 171
14. [14]
  [14] Li X Y, Wang F G, Pan X L, Bao X H. Chin J Catal (李星运, 王发根, 潘秀莲, 包信和. 催化学报), 2013, 34: 257
15. [15]
  [15] Liu H T, Li S Q, Zhang S B, Wang J M, Zhou G J, Chen L, Wang X L. Catal Commun, 2008, 9: 51
16. [16]
  [16] Wang Y W, Guo X N, Dong L L, Jin G Q, Wang Y Y, Guo X Y. Int J Hydrogen Energy, 2013, 38: 12733
17. [17]
  [17] Zhang G Q, Peng J X, Sun T J, Wang S D. Chin J Catal (张国权, 彭家喜, 孙天军, 王树东. 催化学报), 2013, 34: 1745
18. [18]
  [18] Li H L, Lei Y G, Huang Y, Fang Y P, Xu Y H, Zhu L, Li X. J Nat Gas Chem, 2011, 20: 145
19. [19]
  [19] Jiao Z F, Guo X N, Zhai Z Y, Jin G Q, Wang X M, Guo X Y. Catal Sci Technol, 2014, 4: 2494
1. [1]
  Wenjiang LI , Pingli GUAN , Rui YU , Yuansheng CHENG , Xianwen WEI . C₆₀-MoP-C nanoflowers van der Waals heterojunctions and its electrocatalytic hydrogen evolution performance. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 771-781. doi: 10.11862/CJIC.20230289
2. [2]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
3. [3]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
4. [4]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
5. [5]
  Huimin Liu , Kezhi Li , Xin Zhang , Xuemin Yin , Qiangang Fu , Hejun Li . SiC Nanomaterials and Their Derived Carbons for High-Performance Supercapacitors. Acta Physico-Chimica Sinica, 2024, 40(2): 2304026-0. doi: 10.3866/PKU.WHXB202304026
6. [6]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
7. [7]
  Nan Xiao , Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099
8. [8]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
9. [9]
  Zhongyan Cao , Youzhi Xu , Menghua Li , Xiao Xiao , Xianqiang Kong , Deyun Qian . Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes. University Chemistry, 2025, 40(4): 277-281. doi: 10.12461/PKU.DXHX202407017
10. [10]
  Xiyuan Zhang , Rui Dong , Yang Yang , Jiapeng Ding , Zhiwei Miao . Palladium-Catalyzed Tandem Cyclization of 4-Vinylbenzoxazinone and Indene-2-carbaldehyde: A Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(9): 361-367. doi: 10.12461/PKU.DXHX202410062
11. [11]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
12. [12]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
13. [13]
  Qi Wang , Yuqing Liu , Jiefei Wang , Yuan-Yuan Ma , Jing Du , Zhan-Gang Han . Catalysts for electrocatalytic dechlorination of chlorinated aromatic hydrocarbons: synthetic strategies, applications, and challenges. Acta Physico-Chimica Sinica, 2025, 41(10): 100120-0. doi: 10.1016/j.actphy.2025.100120
14. [14]
  Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
15. [15]
  Xiting Zhou , Zhipeng Han , Xinlei Zhang , Shixuan Zhu , Cheng Che , Liang Xu , Zhenyu Sun , Leiduan Hao , Zhiyu Yang . Dual Modulation via Ag-Doped CuO Catalyst and Iodide-Containing Electrolyte for Enhanced Electrocatalytic CO₂ Reduction to Multi-Carbon Products: A Comprehensive Chemistry Experiment. University Chemistry, 2025, 40(7): 336-344. doi: 10.12461/PKU.DXHX202412070
16. [16]
  Xiaowu Zhang , Pai Liu , Qishen Huang , Shufeng Pang , Zhiming Gao , Yunhong Zhang . Acid-Base Dissociation Equilibrium in Multiphase System: Effect of Gas. University Chemistry, 2024, 39(4): 387-394. doi: 10.3866/PKU.DXHX202310021
17. [17]
  Haoyu Sun , Dun Li , Yuanyuan Min , Yingying Wang , Yanyun Ma , Yiqun Zheng , Hongwen Huang . Hierarchical Palladium-Copper-Silver Porous Nanoflowers as Efficient Electrocatalysts for CO₂ Reduction to C₂₊ Products. Acta Physico-Chimica Sinica, 2024, 40(6): 2307007-0. doi: 10.3866/PKU.WHXB202307007
18. [18]
  Jiarui Wu , Gengxin Wu , Yan Wang , Yingwei Yang . Crystal Engineering Based on Leaning Towerarenes. University Chemistry, 2024, 39(3): 58-62. doi: 10.3866/PKU.DXHX202304014
19. [19]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044
20. [20]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039

Get Citation

PDF

XML

Metrics

PDF Downloads(199)
Abstract views(921)
HTML views(80)

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