Citation: Ai Feng, Xie Zongbo, Jiang Guofang, Ji Jiujian, Le Zhanggao. Benzylic C(sp³)-H Functionalization Reaction of 2-Methylazaarenes in Ionic Liquid Aqueous Solution[J]. Chinese Journal of Organic Chemistry, ;2018, 38(8): 2174-2181. doi: 10.6023/cjoc201802012 shu

Benzylic C(sp³)-H Functionalization Reaction of 2-Methylazaarenes in Ionic Liquid Aqueous Solution

Department of Applied Chemistry, East China University of Technology, Nanchang 330013

Corresponding author: Xie Zongbo, zbxie@ecit.cn Le Zhanggao, zhgle@ecit.cn
Received Date: 7 February 2018
Revised Date: 16 March 2018
Available Online: 13 August 2018
Fund Project: the National Natural Science Foundation of China 21462001the National Natural Science Foundation of China 21262002Project supported by the National Natural Science Foundation of China (Nos. 21462001, 21262002, 21465002), the Science and Technology Projects of Jiangxi Province (No. 20161BCB24006) and the Science and Technology Foundation of the Jiangxi Education Department (Nos. KJLD14050, GJJ150584)the Science and Technology Projects of Jiangxi Province 20161BCB24006the Science and Technology Foundation of the Jiangxi Education Department GJJ150584the Science and Technology Foundation of the Jiangxi Education Department KJLD14050the National Natural Science Foundation of China 21465002

Figures(1)

The catalyst-free addition of 2-methylazaarenes benzylic C(sp³)-H to electron-deficient olefins in neutral ionic liquid aqueous solution was reported, and a series of azaarene derivatives were obtained in good yields. This method is easy to operate and the reaction conditions are mild, which not only expands the application of ionic liquid in C(sp³)-H functionalization reaction, but also has positive significance for promoting the development of the green chemistry.
- ionic liquid aqueous solution,
- electron-deficient olefin,
- benzylic C(sp³)-H functionalization,
- 2-methylazaarene
1. [1]
  (a) Duanmu, D. -D. ; Liang, B. -J. ; Jiang, Q. -B. ; Yan, H. Chin. J. Org. Chem. 2017, 37, 2669 (in Chinese).
  (端木丹丹, 梁柏健, 蒋其柏, 燕红, 有机化学, 2017, 37, 2669. )
  (b) Joshua, R. -H. ; Jeffrey, A. -B. ; Jonathan, A. -E. Chem. Rev. 2017, 117, 9163.
  (c) Yang, L. ; Huang, H. M. Chem. Rev. 2015, 115, 3468.
  (d) Yan, G. M. ; Wu, X. M. ; Yang, M. H. Org. Biomol. Chem. 2013, 11, 5558.
  (e) Qian, B. ; Guo, S. M. ; Shao, J. P. ; Zhu, Q. M. ; Yang, L. ; Xia, C. G. ; Huang, H. M. J. Am. Chem. Soc. 2010, 132, 3650.
2. [2]
  (a) Tobisu, M. ; Chatani, N. Angew. Chem. , Int. Ed. 2006, 45, 1683.
  (b) Campos, K. -R. Chem. Soc. Rev. 2007, 36, 1069.
  (c) Jazzar, R. ; Hitce, J. ; Renaudat, A. ; Sofack-Kreutzer, J. ; Baudoin, O. Chem. -Eur. J. 2010, 16, 2654.
  (d) Ramirez, T. -A. ; Zhao, B. ; Shi, Y. Chem. Soc. Rev. 2012, 41, 931.
3. [3]
  (a) Behr, J. -B. ; Gourlain, T. ; Helimi, A. ; Guillerm, G. Bioorg. Med. Chem. Lett. 2003, 13, 1713.
  (b) Heasley, B. H. ; Jarosz, R. ; Carter, K. M. ; Jenny, V. S. ; Lynch, K. R. ; Macdonald, T. L. Bioorg. Med. Chem. Lett. 2004, 14, 4069.
4. [4]
  (a) Landa, A. ; Minkkila, A. ; Blay, G. ; Jergensen, K. A. Chem. -Eur. J. 2006, 12, 3472.
  (b) Woods, C. R. ; Benaglia, M. ; Siegel, J. S. ; Cozzi, F. Angew. Chem. , Int. Ed. 1996, 35, 1830.
  (c) Puglisi, A. ; Benaglia, M. ; Annunziata, R. ; Bologna, A. Tetrahedron Lett. 2003, 44, 2947.
  (d) Chinchilla, R. ; Najera, C. ; Yus, M. Chem. Rev. 2004, 104, 2667.
5. [5]
  (a) Chiu, Y. -H. ; Dos, S. O. ; Canary, J. W. Tetrahedron 1999, 55, 12069.
  (b) Pickaert, G. ; Cesario, M. ; Ziessel, R. J. Org. Chem. 2004, 69, 5335.
  (c) Ziessel, R. ; Pickaert, G. ; Camerel, F. ; Donnio, B. ; Guillon, D. ; Cesario, M. ; Prangé, T. J. Am. Chem. Soc. 2004, 126, 12403.
  (d) Zhu, Y. ; Pavlos, C. M. ; Toscano, J. P. ; Dore, T. M. J. Am. Chem. Soc. 2006, 128, 4267.
6. [6]
  (a) Mori, K. ; Kawasaki, T. ; Akiyama, T. Org. Lett. 2012, 14, 1436.
  (b) Zhang, S. -Y. ; Tu, Y. -Q. ; Fan, C. -A. ; Zhang, F. -M. ; Shi, L. Angew. Chem., Int. Ed. 2009, 121, 8917.
  (c) Blocker, M. ; Immaneni, S. ; Shaikh, A. Tetrahedron Lett. 2014, 55, 5572.
7. [7]
  (a) Gao, X. ; Zhang, F. ; Deng, G. ; Li, Y. Org. Lett. 2014, 16, 3664.
  (b) Jin, T. ; Himuro, M. ; Yamamoto, Y. J. Am. Chem. Soc. 2010, 132, 5590.
  (c) Niu, R. ; Xiao, J. ; Liang, T. ; Li, X. Org. Lett. 2012, 14, 676.
8. [8]
  Dai, S.; Ju, Y.-H.; Barnes, C.-E. J. Chem. Soc., Dalton. Trans. 1999, 8, 1201.
9. [9]
  (a) Wei, G. -T. ; Yang, Z. ; Chen, C. -J. Anal. Chim. Acta 2003, 488, 183.
  (b) Visser, A. -E. ; Jensen, M. -P. ; Laszak, I. Inorg. Chem. 2003, 42, 2197.
10. [10]
  Visser, A.-E.; Rogers, R.-D. J. Solid. State. Chem. 2003, 171, 109. doi: 10.1016/S0022-4596(02)00193-7
11. [11]
  (a) Luo, H. ; Dai, S. ; Bonnesen, P. -V. Anal. Chem. 2004, 76, 3078.
  (b) Han, X. ; Armstrong, D. -W. Acc. Chem. Res. 2007, 40, 1079.
12. [12]
  (a) Zhang, C. -Y. ; Shi, R. -B. ; Chen, C. -Y. ; Jin, C. -M. Chin. J. Org. Chem. 2013, 33, 611 (in Chinese).
  (张传越, 石若冰, 陈才元, 金传明, 有机化学, 2013, 33, 611. )
  (b) Li, J. X. ; Yang, S. R. ; Wu, W. Q. ; Jiang, H. F. Eur. J. Org. Chem. 2018, 1284.
  (c) Li, J. X. ; Li, C. ; Ouyang, L. ; Li, C. S. ; Wu, W. Q. ; Jiang, H. F. Org. Biomol. Chem. 2017, 15, 7898.
  (d) Li, J. X. ; Li, C. ; Ouyang, L. ; Li, C. S. ; Yang, S. R. ; Wu, W. Q. ; Jiang, H. F. Adv. Synth. Catal. 2018, 360, 1138.
13. [13]
  Xu, J.-M.; Wu, Q.; Zhang, Q.-Y.; Zhang, F.; Lin, X.-F. Eur. J. Org. Chem. 2007, 1798.
14. [14]
  (a) Nobuoka, K. ; Kitaoka, S. ; Kunimitsu, K. ; Iio, M. ; Harran, T. ; Wakisaka, A. ; Ishikawa, Y. J. Org. Chem. 2005, 70, 10106.
  (b) Kumar, A. ; Pawar, S. S. J. Org. Chem. 2007, 72, 8111.
15. [15]
  Gruttadauria, M.; Riela, S.; Aprile, C.; Meo, P. L.; Anna, F. D.; Noto, R. Adv. Synth. Catal. 2006, 348, 82. doi: 10.1002/(ISSN)1615-4169
16. [16]
  Xin, X.; Guo, X.; Duan, H.-F.; Lin, Y.-J.; Sun, H. Catal. Commun. 2007, 8, 115.
17. [17]
  Zhao, X.-L.; Liu, L.; Chen, Y.-J.; Wang, D. Tetrahedron 2006, 62, 7113. doi: 10.1016/j.tet.2006.04.075
18. [18]
  (a) Law, M. C. ; Cheung, T. W. ; Wong, K. Y. ; Chan, T. H. J. Org. Chem. 2007, 72, 923.
  (b) Xiao, Y. ; Malhotra, S. V. J. Organomet. Chem. 2005, 690, 3609.
19. [19]
  (a) Conte, V. ; Floris, B. ; Galloni, P. ; Mirruzzo, V. ; Scarso, A. ; Sordi, D. ; Strukul, G. Green Chem. 2005, 7, 262.
  (b) Paul, F. Coord. Chem. Rev. 2000, 203, 269.
20. [20]
  Lei, Z.-L.; Chen, B.-H.; Li, C.-Y.; Liu, H. Chem. Rev. 2008, 108, 1419. doi: 10.1021/cr068441+
21. [21]
  Li, H.-Y.; Xing, L.-J.; Xu, T.; Wang, P. Tetrahedron Lett. 2013, 54, 858. doi: 10.1016/j.tetlet.2012.11.100
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沈阳化工大学材料科学与工程学院沈阳 110142

Benzylic C(sp3)-H Functionalization Reaction of 2-Methylazaarenes in Ionic Liquid Aqueous Solution

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通讯作者: 陈斌, bchen63@163.com

Benzylic C(sp³)-H Functionalization Reaction of 2-Methylazaarenes in Ionic Liquid Aqueous Solution