SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 11: 3207 - 3214

DOI: https://doi.org/10.6023/cjoc201904069

An Efficient Palladium Nanoparticles Catalytic System for Suzuki Coupling Reactions

  • Hengchao Li ,
  • Ling Zhao ,
  • Yan Liu ,
  • Xia Zhang ,
  • Wangbing Li ,
  • Linhai Jing ,
  • Jin Huang ,
  • Wei Wang
Expand
  • Chemical Synthesis Pollution Control Key Laboratory of Sichuan, Province Institute of Applied Chemistry, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong, Sichuan 637002

Received date: 2019-04-27

  Online published: 2019-07-03

Supported by

the National Natural Science Foundation of China(21602144);the Sichuan Science and Technology Program(2018JY0485);the Fundamental Research Funds of China West Normal University(17E049)

Fold

Abstract

A simple and highly efficient palladium nanoparticles catalytic system was applied in Suzuki coupling reaction. This system could catalyze a variety of aryl halide and arylboronic acid substrates with a wide range of functional groups. A high turnover number of 90000 was obtained with the catalyst loading as low as 0.001 mol%. This catalyst system exhibited good stability and longevity.

Key words： aryl hailde; arylboronic acid; palladium nanoparticle; Suzuki coupling

Cite this article

Hengchao Li , Ling Zhao , Yan Liu , Xia Zhang , Wangbing Li , Linhai Jing , Jin Huang , Wei Wang . An Efficient Palladium Nanoparticles Catalytic System for Suzuki Coupling Reactions[J]. Chinese Journal of Organic Chemistry, 2019 , 39(11) : 3207 -3214 . DOI: 10.6023/cjoc201904069

References

[1] Miyaura N.; Suzuki A. Chem. Rev. 1995, 95 2457.
[2] Suzuki A. Chem. Commun. 2005 4759.
[3] Suzuki A. Angew. Chem., Int. Ed. 2011, 50 6722.
[4] Capdeville R.; Buchdunger E.; Zimmermann J.; Matter A. Nat. Rev. Drug Discovery 2002, 1 493.
[5] Corbet J. P.; Mignani G. Chem. Rev. 2006, 106 2651.
[6] Magano J.; Dunetz J. R. Chem. Rev. 2011, 111 2177.
[7] Fihri A.; Bouhrara M.; Nekoueishahraki B.; Basset J.-M.; Polshettiwar V. Chem. Soc. Rev. 2011, 40 5181.
[8] (a) Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417.
[8] (b) Stockton, K. P.; Merritt, C. J.; Sumby, C. J.; Greatrex, B. W. Eur. J. Org. Chem. 2015, 6999.
[8] (c) Li, J.-X.; Yang, S.-R.; Wu, W.-Q.; Jiang, H.-F. Eur. J. Org. Chem. 2018, 1284.
[9] Albisson D. A.; Bedford R. B.; Lawrence S. E.; Scully P. N. Chem. Commun. 1998 2095.
[10] Zapf A.; Ehrentraut A.; Beller M. Angew. Chem., Int. Ed. 2000, 39 4153.
[11] Yuan D.; Huynh H. V. Organometallics 2010, 29 6020.
[12] Bianchini C.; Lee H. M.; Meli A.; Oberhauser W.; Vizza F.; Brüggeller P.; Rainer H. B.; Langes C. Chem. Commun. 2000 777.
[13] Nair P.; Anderson G. K.; Rath N. P. Organometallics 2003, 22 1494.
[14] Imamoto T.; Yashio K.; Crépy K. V. L.; Katagiri K.; Takahashi H.; Kouchi M.; Gridnev I. D. Organometallics 2006, 25 908.
[15] Field L. D.; Messerle B. A.; Smernik R. J.; Hambley T. W.; Turner P. Inorg. Chem. 1997, 36 2884.
[16] (a) Laurenti, D.; Feuerstein, M.; Pèpe, G.; Doucet, H.; Santelli, M. J. Org. Chem. 2001, 66, 1633.
[16] (b) Feuerstein, M.; Laurenti, D.; Bougeant, C.; Doucet, H.; Santelli, M. Chem. Commun. 2001, 325.
[16] (c) Feuerstein, M.; Doucet, H.; Santelli, M. Synlett 2001, 9, 1458.
[16] (d) Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2001, 42, 6667.
[16] (e) Feuerstein, M.; Doucet, H.; Santelli, M. J. Organomet. Chem. 2003, 687, 327.
[17] Hierso J.-C.; Fihri A.; Amardeil R.; Meunier P.; Doucet H.; Santelli M.; Donnadieu B. Organometallics 2003, 22 4490.
[18] Zaborova E.; Deschamp J.; Guieu S.; Bleriot Y.; Poli G.; Menand M.; Madec D.; Prestat G.; Sollogoub M. Chem. Commun. 2011, 47 9206.
[19] (a) Wang, K.; Yi, T.; Yu, X.-J.; Zheng, X.-L.; Fu, H.-Y.; Chen, H.; Li, R.-X. Appl. Organomet. Chem. 2012, 26, 342.
[19] (b) Wang, K.; Fu, Q.; Zhou, R.; Zheng, X.-L.; Fu, H.-Y.; Chen, H.; Li, R.-X. Appl. Organomet. Chem. 2013, 27, 232.
[19] (c) Wang, K.; Wang, W.; Luo, H.; Zheng, X.-L.; Fu, H.-Y.; Chen, H.; Li, R.-X. Catal. Lett. 2013, 143, 1214.
[19] (d) Guo, F.-C.; Zhou, R.; Jiang, Z.-J.; Wang, W.; Zheng, X.-L.; Fu, H.-Y.; Chen, H.; Li, R.-X. Catal. Commun. 2015, 66, 87.
[20] (a) Bernhardt, E.; Willner, H.; Jonas, V.; Thiel, W.; Aubke, F. Angew. Chem., Int. Ed. 2000, 39, 165.
[20] (b) Sayah, R.; Glegola, K.; Framery, E.; Dufaud, V. Adv. Synth. Catal. 2007, 349, 373.
[20] (c) Gholinejad, M.; Hamed F.; Biji, P. Dalton Trans. 2015, 44, 14293.
[20] (d) Zhang, Q.; Li, J.-H.; Zhao, X. Chin. J. Org. Chem. 2016, 36, 130 (in Chinese).
[20] (张强, 李继航赵鑫, 有机化学, 2016, 36, 130.)
[20] (e) Yang, P.-B.; Ma, R.; Bian, F.-L. ChemCatChem 2016, 8, 3746.
[20] (f) Sharma, S.; Nazir, R.; Pande, S.; Sarkar, B. R. ChemistrySelect 2017, 2, 8745.
[20] (g) Kunfi, A.; May, Z.; Németh, P.; London, G. J. Catal. 2018, 361, 84.
[20] (h) Liu, X.-M.; Tang, B.; Long, J.-L.; Zhang, W.; Liu, X. H.; Mirza, Z. Sci. Bull. 2018, 63, 502.
[20] (i) Fu, Y.-F.; Zou, Z.-J.; Tang, C.; Song, K.-P. Chin. J. Org. Chem. 2018, 38, 3106 (in Chinese).
[20] (付玉芳, 邹志娟, 唐成, 宋昆鹏, 有机化学, 2018, 38, 3106.)
[20] (j) Narkhede, N.; Uttam, B.; Rao, C. P. ACS Omega 2019, 4, 4908.
[21] (a) Wang, W.; Yang, Q.; Zhou, R.; Fu, H.-Y.; Zheng, X.-L.; Chen, H.; Li, R.-X. J. Organomet. Chem. 2012, 697, 1.
[21] (b) Wang, W.; Zhou, R.; Jiang, Z.-J.; Wang, K.; Fu, H.-Y.; Zheng, X.-L.; Chen, H.; Li, R.-X. Adv. Synth. Catal. 2014, 356, 616.
[21] (c) Wang, W.; Zhou, R.; Jiang, Z.-J.; Wang, X.; Fu, H.-Y.; Zheng, X.-L.; Chen, H.; Li, R.-X. Eur. J. Org. Chem. 2015, 2579.
[21] (d) Huang, J.; Fu, R.-H.; Jing, L.-H.; Qin, D.-B.; Huang, K.; Wang, W. Chin. J. Org. Chem. 2019, 39, 456 (in Chinese).
[21] (黄锦, 付荣辉, 敬林海, 秦大斌, 黄昆, 汪伟, 有机化学, 2019, 39, 456.)
[21] (e) He, H.-Y.; Wang, W.; Yu, X.-J.; Huang, J.; Jian, L.; Fu, H.-Y.; Zheng, X.-L.; Chen, H.; Li, R.-X. Eur. J. Org. Chem. 2016, 56169.
[22] Arumugam V.; Kaminsky W.; Bhuvanesh N. S. P.; Nallasamy D. RSC Adv. 2015, 5 59428.
[23] Lysén M.; K?hler K. Synthesis 2006, 4 692.
[24] Jansa J.; Jambor R. Appl. Organomet. Chem. 2016, 30 1036.
[25] Ahmed J.; Chakraborty S.; Jose A.; Mandal S. K. J. Am. Chem. Soc. 2018, 140 8330.
[26] Klein M.; Voigtmann U.; Haack T.; Erdinger L.; Boche G. Mutat. Res. 2000, 467 55.
[27] Macé Y.; Raymondeau B.; Pradet C.; Blazejewski J. C.; Magnier E. Eur. J. Org. Chem. 2009 1390.
[28] Ernst J. B.; Rakers L.; Glorius F. Synthesis 2017, 49 260.
[29] Duan X.-Y.; Li P.-B.; Zhu G.-R.; Fu C.-L.; Chen Q.; Huang X.; Ma S.-M. Org. Chem. Front. 2018, 5 3319.
[30] Chiu C. C.; Chiu H. T.; Lee D. S.; Lu T. J. RSC Adv. 2018, 8 26407.
Options
Outlines

/

〈 〉