Citation: Bai Lili, Wang Ying, Wang Shuojin, Kong Dulin, Fu Yan, Peng Deqian, Wen Lijun, Chen Xun. Ruthenium(Ⅱ)-Catalyzed C-H Bond Regioselective[3+2] Annulation of Arylamines with Propargyl Alcohols[J]. Chinese Journal of Organic Chemistry, ;2018, 38(12): 3242-3249. doi: 10.6023/cjoc201806039 shu

Ruthenium(Ⅱ)-Catalyzed C-H Bond Regioselective[3+2] Annulation of Arylamines with Propargyl Alcohols

School of Pharmacy, Hainan Medical University, Haikou 571199

Corresponding author: Peng Deqian, pengdeqian2004@163.com Chen Xun, chenxunchenpei@163.com
Received Date: 25 June 2018
Revised Date: 23 July 2018
Available Online: 23 December 2018
Fund Project: Project supported by the Program of Hainan Association for Science and Technology Plans to Youth R & D Innovation (Nos. QCXM201808, QCXM201707)the Program of Hainan Association for Science and Technology Plans to Youth R & D Innovation QCXM201808the Program of Hainan Association for Science and Technology Plans to Youth R & D Innovation QCXM201707

Figures(4)

A simple and efficient ruthenium(Ⅱ)-catalyzed C-H bond regioselective[3+2] annulation of arylamines with propargyl alcohols has been reported. This protocol provides a facile approach to hydroxy-containing indole skeleton, which could be employed for constructing more complex and useful pharmaceutical molecules. Meantime, the kinetic isotope effect was further investigated and the results indicated that the C-H bond-breaking was possibly involved in the rate-limiting step of this transformation.
- ruthenium(Ⅱ),
- C-H bond,
- regioselective,
- annulation reaction
1. [1]
  (a) Smart, B. P.; Oslund, R. C.; Walsh, L. A.; Gelb, M. H. J. Med. Chem. 2006, 49, 2858.
  (b) Hu, W.; Guo, Z.; Chu, F.; Bai, A.; Yi, X.; Cheng, G.; Li, J. Bioorg. Med. Chem. 2003, 11, 1153.
  (c) Somei, M.; Yamada, F. Nat. Prod. Rep. 2005, 22, 73. (d) Kaushik, N.; Kaushik, N.; Attri, P.; Kumar, N.; Kim, C.; Verma, A.; Choi, E. Molecules 2013, 18, 6620.
2. [2]
  (a) Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489.
  (b) Alexandre, F. R.; Amador, A.; Bot, S.; Caillet, C.; Convard, T.; Jakubik, J.; Musiu, C.; Poddesu, B.; Vargiu, L.; Liuzzi, M.; Roland, A.; Seifer, M.; Standring, D.; Storer, R.; Dousson, C. B. J. Med. Chem. 2011, 54, 392.
  (c) Chiu, C. W.; Chow, T. J.; Chuen, C. H.; Lin, H. M.; Tao, Y. T. Chem. Mater. 2003, 15, 4527.
3. [3]
  (a) Reissert, A. Ber. Dtsch. Chem. Ges. 1897, 30, 1030.
  (b) Batcho, A. D.; Leimgruber, W. Org. Synth. 1985, 63, 214.
  (c) Patrick, J. B.; Saunders, E. K. Tetrahedron Lett. 1979, 4009.
  (d) Gassman, P. G.; Roos, J. J.; Lee, S. J. J. Org. Chem. 1984, 49, 717.
  (e) Furstner, A.; Ernst, A. Tetrahedron 1995, 51, 773.
4. [4]
  Fischer, E.; Jourdan, F. Ber. Dtsch. Chem. Ges. 1883, 16, 2241. doi: 10.1002/(ISSN)1099-0682
5. [5]
  Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689. doi: 10.1021/ja00017a059
6. [6]
7. [7]
  (a) Song, G.; Li, X. Acc. Chem. Res. 2015, 48, 1007.
  (b) Ackermann, L. Acc. Chem. Res. 2014, 47, 281.
  (c) Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651.
8. [8]
  (a) Liu, B.; Song, C.; Sun, C.; Zhou, S.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 16625.
  (b) Wang, C.; Huang, Y. Org. Lett. 2013, 15, 5294.
  (c) Liang, Y.; Jiao, N. Angew. Chem., Int. Ed. 2016, 55, 4035.
  (d) Ackermann, L.; Lygin, A. V. Org. Lett. 2012, 14, 764.
9. [9]
  (a) Han, Y.-P.; Song, X.-R.; Qiu, Y.-F.; Zhang, H.-R.; Li, L.-H.; Jin, D.-P.; Sun, X.-Q.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2016, 18, 940.
  (b) Hosseyni, S.; Su, Y.; Shi, X. Org. Lett. 2015, 17, 6010.
  (c) Song, X.-R.; Han, Y.-P.; Qiu, Y.-F.; Qiu, Z.-H.; Liu, X.-Y.; Xu, P.-F.; Liang, Y.-M. Chem.-Eur. J. 2014, 20, 12046.
  (d) Zhang, X.; Teo, W. T.; Sally; Chan, P. W. H. J. Org. Chem. 2010, 75, 6290.
10. [10]
  Sen, M.; Dahiya, P.; Premkumar, J. R.; Sundararaju, B. Org. Lett. 2017, 19, 3699. doi: 10.1021/acs.orglett.7b01415
11. [11]
  (a) Chen, X.; Xie, Y.; Xiao, X.; Li, G.; Deng, Y.; Jiang, H.; Zeng, W. Chem. Commun. 2015, 51, 15328.
  (b) Chen, X.; Hu, X.; Bai, S.; Deng, Y.; Jiang, H.; Zeng, W. Org. Lett. 2016, 18, 192.
  (c) Chen, X.; Hu, X.; Deng, Y.; Jiang, H.; Zeng, W. Org. Lett. 2016, 18, 4742.
  (d) Hu, X.; Chen, X.; Shao, Y.; Xie, H.; Li, G.; Deng, Y.; Ke, Z.; Jiang, H.; Zeng, W. ACS Catal. 2018, 8, 1308.
12. [12]
  (a) Ackermann, L.; Lygin, A. V. Org. Lett. 2012, 14, 764;
  (b) Wei, L.-M.; Wei, L.-L.; Pan, W.-B.; Wu, M.-J. Tetrahedron Lett. 2003, 44, 595.
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