Notes

Nickel-Catalyzed Coupling of Grignard Reagents and Diaryl Acetylenes for Synthesis of Tetra-substituted Naphthalenes

  • Chen Jinyang ,
  • Wu Xiaobo ,
  • Yi Rongnan ,
  • Xu Xinxua
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  • a. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
    b. Fiber Inspection Bureau of Hubei Province, Wuhan 420100

Received date: 2016-12-24

  Revised date: 2017-02-21

  Online published: 2017-03-14

Supported by

Project supported by the Hunan Provincal Science and Technology Major Projects (No.2014FJ1010).

Abstract

A novel approach for the synthesis of tetra-substituted naphthalenes is demonstrated through the ligand-free coupling of a wide range of alkynes with Grignard reagents catalyzed by NiCl2, avoiding the use of special ligands and expensive catalysts used in previous methods. Other outstanding features include mild reaction conditions, good yields and wide functional group tolerance. The protocol provides an efficient method for the synthesis of highly substituted naphthalenes.

Cite this article

Chen Jinyang , Wu Xiaobo , Yi Rongnan , Xu Xinxua . Nickel-Catalyzed Coupling of Grignard Reagents and Diaryl Acetylenes for Synthesis of Tetra-substituted Naphthalenes[J]. Chinese Journal of Organic Chemistry, 2017 , 37(7) : 1850 -1854 . DOI: 10.6023/cjoc201612057

References

[1] Chiang, C. K.; Fincher, C. R.; Park, Y. W.; Heeger, A. J.; Shirakawa, H.; Louis, E. J.; Gau, S. C.; MacDiarmid, A. G. Phys. Rev. Lett. 1977, 39, 1098
[2] Anthony, J. E. Angew. Chem., Int. Ed. 2008, 47, 452.
[3] Wu, W.; Liu, Y.; Zhu, D. Chem. Soc. Rev. 2010, 39, 1489.
[4] Zhang, J. L.; Xiao, C.; Zhai, L. J.; Wang, X. J.; Bi, F. Q.; Wang, B. Z. Chin. J. Org. Chem. 2016, 36, 1197(in Chinese). (张俊林, 肖川, 翟连杰, 王锡杰, 毕福强, 王伯周, 有机化学, 2016, 36, 1197.)
[5] Wu, J.; Kong, H. H.; Ding, M. W. Chin. J. Org. Chem. 2016, 36, 1662(in Chinese). (武静, 孔晗晗, 丁明武, 有机化学, 2016, 36, 1662.)
[6] Yang, R.; Cai, X. D.; Ding, L. M. Acta Chim. Sinica 2015, 73, 281(in Chinese). (杨瑞, 蔡雪刁, 丁黎明, 化学学报, 2015, 73, 281.)
[7] Ge, T.; Song, J.; yYao, Z. G.; Xu, F. Chin. J. Org. Chem. 2015, 35, 1570(in Chinese). (葛恬, 宋洁, 姚志刚, 徐凡, 有机化学, 2015, 35, 1570.)
[8] Gong, X.; Xie, X.; Chen, N.; Zheng, C.; Zhu, J.; Chen, R.; Huang, W.; Gao, D. Chin. J. Chem. 2015, 33, 967.
[9] Wang, L.; Wang, L.; Huang, J.; Yu, G. Chin. J. Chem. 2015, 33, 948.
[10] Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99.
[11] Narasimhan, N. S.; Bapat, C. P. J. Chem. Soc., Perkin Trans. 11984, 1435.
[12] Wang, C.; Dong, H.; Hu, W.; Liu, Y.; Zhu, D. Chem. Rev. 2012, 112, 2208.
[13] Murphy, A. R.; Frechet, J. M. J. Chem. Rev. 2007, 107, 1066.
[14] Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B. Nature 1990, 347, 539.
[15] Coakley, K. M.; McGehee, M. D. Chem. Mater. 2004, 16, 4533
[16] Someya, T.; Katz, H. E.; Gelperin, A.; Lovinger, A. J.; Dodabalapur, A. Appl. Phys. Lett. 2002, 81, 3079.
[17] Katz, H. E.; Bao, Z. J. Phys. Chem. B 2000, 104, 671.
[18] Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891.
[19] Kaur, I.; Stein, N. N.; Kopreski, R. P.; Miller, G. P. J. Am. Chem. Soc 2009, 131, 3424.
[20] Ahmed, E.; Briseno, A. L.; Xia, Y.; Jenekhe, S. A. J. Am. Chem. Soc. 2008, 130, 1118.
[21] Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2011, 76, 2867.
[22] Takahashi. T.; Li, Y.; Stepnicja, P.; Kitamura, M.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 576.
[23] Umeda, N.; Tsurugi, H.; Satoh, T.; Miera, M. Angew. Chem., Int. Ed. 2008, 47, 4019.
[24] Takahashi, T.; Kitamura, M.; Shen, B.; Nakajima, K. J. Am. Chem. Soc. 2000, 122, 12876.
[25] Bennett, M. A.; Hockless, C. R.; Wenger, E. Organometallics 1995, 14, 2091.
[26] Bowles, D. M.; Anthony, J. E. Org. Lett. 2000, 2, 85.
[27] Kawasaki, S.; Satoh, T.; Miura, M.; Nomura, M. J. Org. Chem. 2003, 68, 6836.
[28] Hsieh, J-C.; Cheng, C-H. Chem. Commun. 2008, 2992.
[29] Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2009, 11, 5198.
[30] Uto, T.; Shimazu, M.; Ueura, K.; Tsurugi, H.; Satoh, T.; Miura, M. J. Org. Chem. 2008, 73, 298.
[31] Geng, K.; Fan, Z.; Zhang, A. Org. Chem. Front. 2016, 3, 349.
[32] Ueura, K.; Satoh, T.; Miura, M. J. Org. Chem. 2007, 72, 5362.
[33] Jafarpour, F.; Hazrati, H.; Nouraldinmousa, S. Org. Lett. 2013, 15, 3816.
[34] Cant, A. A.; Roberts, L.; Greaney, M. F. Chem. Commun. 2010, 46, 8671.
[35] Adak, L.; Yoshikai, N. Tetrahedron 2012, 68, 5167.
[36] Ilies, L.; Matsumoto, A.; Kobayashi, M.; Yoshikai, N.; Nakamura, E. Synlett 2012, 23, 2381.
[37] Thakur, K. G.; Sekar, G. Synthesis 2009, 16, 2785.
[38] Wu, Y.-T.; Huang, K.-H.; Shin, C.-C.; Wu, T.-C. Chem.-Eur. J. 2008, 14, 6697.

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