Citation: Jiang Wenjie, Song Yating, Wei Xiaojing, Xu Yi, Lu Juan, Jiang Bo, Hao Wenjuan. C—C Triple Bond Cleavage/Rearrangement Reaction for Accessing 2, 4, 4-Trichloronaphthalen-1(4H)-ones[J]. Chinese Journal of Organic Chemistry, ;2019, 39(4): 1095-1101. doi: 10.6023/cjoc201811015 shu

C—C Triple Bond Cleavage/Rearrangement Reaction for Accessing 2, 4, 4-Trichloronaphthalen-1(4H)-ones

Jiang Wenjie ^a,b ,
Song Yating ^a,b ,
Wei Xiaojing ^a ,
Xu Yi ^a ,
Lu Juan ^a ,
Jiang Bo ^a,b,, ,
Hao Wenjuan ^a

a.
School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou 221116
b.
C. W. Chu College, Jiangsu Normal University, Xuzhou 221116

Corresponding author: Jiang Bo, jiangchem@jsnu.edu.cn
Received Date: 10 November 2018
Revised Date: 7 December 2018
Available Online: 21 April 2018
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21602087), the Top-notch Academic Programs Project of Jiangsu Higher Education Institutions, the Natural Science Foundation of Jiangsu Province (No. BK20160212), and the Qing Lan Project of Jiangsu Education Committeethe Natural Science Foundation of Jiangsu Province BK20160212the National Natural Science Foundation of China 21602087

Figures(3)

N-Chlorosuccinimide (NCS)-mediated[2+2] cycloaddition and C-C triple bond cleavage/rearrangement reaction of yne-allenones and H₂O as a nucleophilic reagent enabled the formation of 18 examples of 2, 4, 4-trichloronaphthalene-1(4H)-one derivatives with 55%~88% yields. The structures of these obtainable products were based on their NMR, IR and HRMS data, among which the structure of product 2e was confirmed by X-ray analysis. This metal-free transformation features mild conditions, simple operation and high reaction yields. It provides an effective and new protocol for the synthesis of trichloro-substituted naphthalene-1(4H)-ones.
- yne-allenones,
- [2+2] cycloaddition,
- C-C triple bond cleavage/rearrangement,
- 2, 4, 4-trichloronaphthalene-1(4H)-ones
1. [1]
  (a) For reviews, see: Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241.
  (b) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870.
2. [2]
  (a) Jiang, Q.; Zhao, A.; Xu, B.; Jia, J.; Liu, X.; Guo, C. J. Org. Chem. 2014, 79, 2709.
  (b) Okamoto, N.; Ishikura, M.; Yanada, R. Org. Lett. 2013, 15, 2571.
3. [3]
  (a) Chamberlin, R. L. M.; Rosenfeld, D. C.; Wolczanski, P. T.; Lobkovsky, E. B. Organometallics 2002, 21, 2724.
  (b) Adams, H.; Guio, L. V. Y.; Morris, M. J.; Spey, S. E. J. Chem. Soc., Dalton Trans. 2002, 2907.
  (c) O'Connor, J. M.; Pu, L. J. Am. Chem. Soc. 1990, 112, 9013.
  (d) Hayashi, N.; Ho, D. M.; Pascal, Jr., R. A. Tetrahedron Lett. 2000, 41, 4261.
  (e) Cairns, G. A.; Carr, N.; Green, M.; Mahon, M. F. Chem. Commun. 1996, 2431.
4. [4]
  (a) Moriarty, R. M. Penmasta, R.; Awasthi, A. K.; Prakash, I. J. Org. Chem. 1988, 53, 6124.
  (b) Sawaki, Y.; Inoue, H.; Ogata, Y. Bull. Chem. Soc. Jpn. 1983, 56, 1133.
  (c) Sullivan, B. P.; Smythe, R. S.; Kober, E. M.; Meyer, T. J. J. Am. Chem. Soc. 1982, 104, 4701.
5. [5]
  Shen, T.; Wang, T.; Qin, C.; Jiao, N.; Angew. Chem., Int. Ed. 2013, 52, 6677. doi: 10.1002/anie.v52.26
6. [6]
  (a) Wang, A.; Jiang, H. J. Am. Chem. Soc., 2008, 130, 5030.
  (b) Liu, Q.; Chen, P.; Liu, G. ACS Catal. 2013, 3, 178.
7. [7]
  (a) Jun, C.-H.; Lee, H.; Moon, C. W.; Hong, H.-S. J. Am. Chem. Soc. 2001, 123, 8600.
  (b) Cha, K.-M.; Jo, E.-A.; Jun, C.-H. Synlett 2009, 2939.
8. [8]
  (a) Das, A.; Chaudhuri, R.; Liu, R.-S. Chem. Commun. 2009, 4046.
  (b) Liu, Y.; Song, F.; Guo, S. J. Am. Chem. Soc. 2006, 128, 11332.
  (c) Qin, C.; Su, Y.; Shen, T.; Shi, X.; Jiao, N. Angew. Chem., Int. Ed. 2016, 55, 350.
9. [9]
  Sun, J.; Wang, F.; Hu, H.; Wang, X.; Wu, H.; Liu, Y. J. Org. Chem. 2014, 79, 3992. doi: 10.1021/jo500456d
10. [10]
  (a) Datta, S.; Chang, C.-L.; Yeh, K.-L.; Liu, R.-S. J. Am. Chem. Soc. 2003, 125, 9294.
  (b) Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 6646.
11. [11]
  (a) Liang, Y.-F.; Song, S.; Ai, L.; Li, X.; Jiao, N. Green Chem. 2016, 18, 6462.
  (b) Sha, H.-K.; Xu, T.; Liu, F.; Tang, B.-Z.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Chem. Commun. 2018, 54, 10415.
  (c) Sha, H.-K.; Liu, F.; Lu, J.; Liu, Z.-Q.; Hao, W.-J.; Tang, J.-L.; Tu, S.-J.; Jiang, B. Green Chem. 2018, 20, 3476.
  (d) Wang, L.; Shi, L.-X.; Liu, L.; Li, Z.-X.; Xu, T.; Hao, W.-J.; Li, G.; Tu, S.-J.; Jiang, B. J. Org. Chem. 2017, 82, 3605
12. [12]
  (a) Qiu, J.-K.; Jiang, B.; Zhu, Y.-L.; Hao, W.-J.; Wang, D.-C.; Sun, J.; Wei, P.; Tu, S.-J.; Li, G. J. Am. Chem. Soc. 2015, 137, 8928.
  (b) Sun, J.; Qiu, J.-K.; Wu, Y.-N.; Hao, W.-J.; Guo, C.; Li, G.; Tu, S.-J.; Jiang, B. Org. Lett. 2017, 19, 754.
  (c) Liu, F.; Wang, J.-Y.; Zhou, P.; Li, G.; Hao, W.-J.; Tu, S.-J.; Jiang B., Angew. Chem., Int. Ed. 2017, 56, 15570.
  (d) Huang, M.-H.; Hao, W.-J.; Li, G.; Tu, S.-J.; Jiang, B. Chem. Commun. 2018, 54, 10791.
  (e) Huang, M.-H.; Hao, W.-J.; Jiang, B. Chem. Asian J. 2018, 13, 2958.
  (f) Wang, A.-F.; Hao, W.-J.; Zhu, Y.-L.; Li, G.; Zhou, P.; Tu, S.-J.; Jiang, B. ACS Omega 2018, 3, 1482.
13. [13]
  (a) Wang, J.-Y.; Zhou, P.; Li, G.; Hao W.-J.; Tu, S.-J.; Jiang, B. Org. Lett. 2017, 19, 6682.
  (b) Zhou, P.; Wang, J.-Y.; Zhang, T.-S.; Li, G.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Chem. Commun. 2018, 54, 164.
  (c) Li, H.; Hao, W.-J.; Wang, M.; Qin, X.; Tu, S.-J.; Zhou, P.; Li, G.; Wang, J.; Jiang, B. Org. Lett. 2018, 20, 4362.
14. [14]
  For selected examples, see: (a) Shen, Q.; G. Hammond, B. J. Am. Chem. Soc. 2002, 124, 6534.
  (b) Ohno, H.; Mizutani, T.; Kadoh, Y.; Miyamura, K.; Tanaka, T. Angew. Chem., Int. Ed. 2005, 44, 5113.
  (c) Siebert, M. R.; Osbourn, J. M.; Brummond, K. M.; Tantillo, D. J. J. Am. Chem. Soc. 2010, 132, 11952.
15. [15]
  Li, H.; Hao, W.-J.; Li, G.; Tu, S.-J.; Jiang, B. Front. Chem. 2018, 6, 599.
  (b) Li, H.; Zhou, P.; Xie, F.; Hu, J.-Q.; Yang, S.-Z.; Wang, Y.-J.; Hao, W.-J.; Tu, S.-J.; Jiang, B. J. Org. Chem. 2018, 83, 13335.
  (c) Wang, J.-Y.; Xie, F.; Hu, J.-Q.; Yang, S.-Z.; Wang, Y.-J.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Org. Biomol. Chem. 2018, 16, 7104.
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