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Chinese Journal of Organic Chemistry >

2017 , Vol. 37 >Issue 10: 2655 - 2662

DOI: https://doi.org/10.6023/cjoc201705014

ARTICLE

Construction of Carbazoles by Palladium-Catalyzed Direct Cross-Coupling of Indoles with in situ Generated Aryl Vinyl Ketones

  • Zhou Quanlong ,
  • Zhu Changlei ,
  • Wu Ge ,
  • Zhang Yuanfei ,
  • Zhang Min ,
  • Su Weiping
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  • a State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002;
    b College of Materials Science and Engineering, Fujian Normal University, Fuzhou 350007

Received date: 2017-05-08

  Revised date: 2017-07-06

  Online published: 2017-08-11

Supported by

Project supported by the National Natural Science Foundation of China (Nos.21431008,21332001,21602221,u1505242).

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Abstract

The synthesis of carbazoles via Pd-catalyzed direct cross-coupling of indoles with in situ generated aryl vinyl ketones by using statured ketones as the olefins source is described. This protocol obviates the need for additional preparation steps of aryl vinyl ketones and therefore opens up a new door to synthesis of carbazoles in an atom-and step-economical fashion.

Key words： palladium-catalyzed; dehydrogenation; carbazoles; C—H functionalization; cross-coupling

Cite this article

Zhou Quanlong , Zhu Changlei , Wu Ge , Zhang Yuanfei , Zhang Min , Su Weiping . Construction of Carbazoles by Palladium-Catalyzed Direct Cross-Coupling of Indoles with in situ Generated Aryl Vinyl Ketones[J]. Chinese Journal of Organic Chemistry, 2017 , 37(10) : 2655 -2662 . DOI: 10.6023/cjoc201705014

References

[1] (a) Zhang, F.-F.; Gan, L.-L.; Zhou, C.-H. Bioorg. Med. Chem. Lett. 2010, 20, 1881.
(b) Blunt, J. W.; Copp, B. R.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. Nat. Prod. Rep. 2003, 20, 1.
(c) Deslandes, S.; Chassaing, S.; Delfourne, E. Mar. Drugs 2009, 7, 754.
(d) Maneerat, W.; Ritthiwigrom, T.; Cheenpracha, S.; Promgool, T.; Yossathera, K.; Deachathai, S.; Phakhodee, W.; Laphookhieo, S. J. Nat. Prod. 2012, 75, 741.
[2] (a) Roy, J.; Jana, A. K.; Mal, D. Tetrahedron 2012, 68, 6099.
(b) Knölker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303.
(c) Schmidt, A. W.; Reddy, K. R.; Knölker, H.-J. Chem. Rev. 2012, 112, 3193.
[3] (a) Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792.
(b) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
(c) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
(d) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
[4] Zhao, J.; Larock, R. C. J. Org. Chem. 2006, 71, 5340.
[5] (a) Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560.
(b) Jordan-Hore, J. A.; Johansson, C. C.; Beck, E. M.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 16184.
(c) Cho, S. H.; Yoon, J.; Chang, S. J. Am. Chem. Soc. 2011, 133, 5996.
(d) Takamatsu, K.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2014, 16, 2892.
[6] (a) Yamashita, M.; Horiguchi, H.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 7481.
(b) Jia, J.; Shi, J.; Zhou, J.; Liu, X.; Song, Y.; Xu, H. E.; Yi, W. Chem. Commun. 2015, 51, 2925.
[7] (a) Ozaki, K.; Zhang, H.; Ito, H.; Lei, A.; Itami, K. Chem. Sci. 2013, 4, 3416.
(b) Verma, A. K.; Danodia, A. K.; Saunthwal, R. K.; Patel, M.; Choudhary, D. Org. Lett. 2015, 17, 3658.
(c) Laha, J. K.; Dayal, N. Org. Lett 2015, 17, 4742.
(d) Chen, S.; Li, Y.; Ni, P.; Huang, H.; Deng, G. J. Org. Lett 2016.
[8] Grimster, N. P.; Gauntlett, C.; Godfrey, C. R.; Gaunt, M. J. Angew. Chem., Int. Ed. 2005, 44, 3125.
[9] Guo, T.; Jiang, Q.; Huang, F.; Chen, J.; Yu, Z. Org. Chem. Front. 2014, 1, 707.
[10] (a) Muzart, J. Eur. J. Org. Chem. 2010, 3779.
(b) Newhouse, T.; Turlik, A.; Chen, Y. Synlett 2016, 27, 331.
[11] (a) Nicolaou, K. C.; Gray, D. L. F.; Montagnon, T.; Harrison, S. T. Angew. Chem., Int. Ed. 2002, 41, 996.
(b) Nicolaou, K. C.; Montagnon, T.; Baran, P. S. Angew. Chem., Int. Ed. 2002, 41, 993.
(c) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y. L. J. Am. Chem. Soc. 2002, 124, 2245.
(d) Uyanik, M.; Akakura, M.; Ishihara, K. J. Am. Chem. Soc. 2009, 131, 251.
(e) Nicolaou, K. C.; Zhong, Y. L.; Baran, P. S. J. Am. Chem. Soc. 2000, 122, 7596.
[12] (a) Bhattacharya, A.; DiMichele, L. M.; Dolling, U. H.; Douglas, A. W.; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 3318.
(b) Walker, D.; Hiebert, J. D. Chem. Rev. 1967, 67, 153.
[13] (a) Diao, T.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 14566.
(b) Gao, W. M.; He, Z. Q.; Qian, Y.; Zhao, J.; Huang, Y. Chem. Sci. 2012, 3, 883.
(c) Diao, T.; Wadzinski, T. J.; Stahl, S. S. Chem. Sci. 2012, 3, 887.
(d) Diao, T.; Pun, D.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 8205.
(e) Bigi, M. A.; White, M. C. J. Am. Chem. Soc. 2013, 135, 7831.
[14] (a) Zhang, M.; Zhang, Y.; Jie, X.; Zhao, H.; Li, G.; Su, W. Org. Chem. Front. 2014, 1, 843.
(b) Wei, Y.; Hu, P.; Zhang, M.; Su, W. Chem. Rev. 2017.
[15] (a) Zhang, M.; Zhou, J.; Kan, J.; Wang, M.; Su, W.; Hong, M. Chem. Commun. 2010, 46, 5455.
(b) Zhou, J.; Wu, G.; Zhang, M.; Jie, X.; Su, W. Chem.-Eur. J. 2012, 18, 8032.
(c) Zhang, M.; Hu, P.; Zhou, J.; Wu, G.; Huang, S.; Su, W. Org. Lett. 2013, 15, 1718.
(d) Shang, Y.; Jie, X.; Zhou, J.; Hu, P.; Huang, S.; Su, W. Angew. Chem. Int. Ed. 2013, 52, 1299.
[16] Jie, X.; Shang, Y.; Zhang, X.; Su, W. J. Am. Chem. Soc. 2016, 138, 5623.
[17] Xiao, B.; Li, Y. M.; Liu, Z. J.; Yang, H. Y.; Fu, Y. Chem. Commun. 2012, 48, 4854.
[18] Klare, H. F.; Oestreich, M.; Ito, J.; Nishiyama, H.; Ohki, Y.; Tatsumi, K. J. Am. Chem. Soc. 2011, 133, 3312.
[19] Taylor, J. E.; Jones, M. D.; Williams, J. M. J.; Bull, S. D. Org. Lett. 2010, 12, 5740.
[20] Qi, T.; Qiu, W.; Liu, Y.; Zhang, H.; Gao, X.; Liu, Y.; Lu, K.; Du, C.; Yu, G.; Zhu, D. J. Org. Chem. 2008, 73, 4638.

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