Chinese Journal of Organic Chemistry >
Benzylic C(sp3)-H Functionalization Reaction of 2-Methylazaarenes in Ionic Liquid Aqueous Solution
Received date: 2018-02-07
Revised date: 2018-03-16
Online published: 2018-04-13
Supported by
Project 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 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.
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
[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] (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.; Bau-doin, O. Chem.-Eur. J. 2010, 16, 2654.
(d) Ramirez, T.-A.; Zhao, B.; Shi, Y. Chem. Soc. Rev. 2012, 41, 931.
[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] (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] (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] (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] (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] Dai, S.; Ju, Y.-H.; Barnes, C.-E. J. Chem. Soc., Dalton. Trans. 1999, 8, 1201.
[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] Visser, A.-E.; Rogers, R.-D. J. Solid. State. Chem. 2003, 171, 109.
[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] (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] Xu, J.-M.; Wu, Q.; Zhang, Q.-Y.; Zhang, F.; Lin, X.-F. Eur. J. Org. Chem. 2007, 1798.
[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] Gruttadauria, M.; Riela, S.; Aprile, C.; Meo, P. L.; Anna, F. D.; Noto, R. Adv. Synth. Catal. 2006, 348, 82.
[16] Xin, X.; Guo, X.; Duan, H.-F.; Lin, Y.-J.; Sun, H. Catal. Com-mun. 2007, 8, 115.
[17] Zhao, X.-L.; Liu, L.; Chen, Y.-J.; Wang, D. Tetrahedron 2006, 62, 7113.
[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] (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] Lei, Z.-L.; Chen, B.-H.; Li, C.-Y.; Liu, H. Chem. Rev. 2008, 108, 1419.
[21] Li, H.-Y.; Xing, L.-J.; Xu, T.; Wang, P. Tetrahedron Lett. 2013, 54, 858.
/
| 〈 |
|
〉 |
