Citation: Wang Hui, Wang Anwei, Xia Zhenzhen, Zhou Weiyou, Sun Zhonghua, Qian Junfeng, He Mingyang. Nickel(Ⅱ)-Catalyzed Aerobic Cross-Dehydrogenative Coupling for the Synthesis of N-Aryl Tetrahydroisoquinolines[J]. Chinese Journal of Organic Chemistry, ;2020, 40(7): 2099-2107. doi: 10.6023/cjoc202004028 shu

Nickel(Ⅱ)-Catalyzed Aerobic Cross-Dehydrogenative Coupling for the Synthesis of N-Aryl Tetrahydroisoquinolines

Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164

Corresponding author: Zhou Weiyou, zhouwy426@126.com
Received Date: 18 April 2020
Revised Date: 4 May 2020
Available Online: 15 May 2020
Fund Project: the Natural Science Foundation of Jiangsu Province No. BK20181461the Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology No. BM2012110the Postgraduate Research & Practice Innovation Program of Jiangsu Province No. KYCX19_1746Project supported by the Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology (No. BM2012110), the Postgraduate Research & Practice Innovation Program of Jiangsu Province (No. KYCX19_1746), and the Natural Science Foundation of Jiangsu Province (No. BK20181461)

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An nickel-catalyzed aerobic cross-dehydrogenative coupling of N-aryl tetrahydroisoquinolines is presented. The catalytic system could tolerate various N-aryl tetrahydroquinoline derivatives and nucleophiles, and the target products could be obtained in good to excellent yields. Compared with reported methods, the protocol uses molecular oxygen as a sustainable oxidant, and provides an effective approach to the synthesis of tetrahydroisoquinoline derivatives under mild and practical conditions.
- cross-dehydrogenative coupling,
- C—H activation,
- nickel,
- molecular oxygen,
- N-aryl tetrahydroisoquinoline
1. [1]
  (a) Mons, E.; Wanner, M. J.; Ingemann, S.; van Maarseveen, J. H.; Hiemstra, H. J. Org. Chem. 2014, 79, 7380.
  (b) Aladesanmi, A. J.; Kelley, C. J.; Leary, J. D. J. Nat. Prod.1983, 46, 127.
  (c) Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341.
  (d) Ye, K.; Ke, Y.; Keshava, N.; Shanks, J.; Kapp, J. A.; Tekmal, R. R.; Petros, J.; Joshi, H. C. Proc. Natl. Acad. Sci. U.S. A. 1998, 95, 1601.
  (e) Zhang, A.; Neumeyer, J. L.; Baldessarini, R. J. Chem. Rev. 2007, 107, 274.
  (f) Pandey, G.; Tiwari, S. K.; Singh, B. Tetrahedron Lett. 2016, 57, 4480.
  (g) Tsang, A. S. K.; Ingram, K.; Keiser, J.; Hibbert, D. B.; Todd, M. H. Org.Biomol. Chem. 2013, 11, 4921.
  (h) Zhang, G.; Zhang, Y.; Wang, R. Angew. Chem., Int. Ed.2011, 50, 10429.
  (i) Gao, M.; Kong, D.; Clearfield, A.; Zheng, Q. H. Bioorg. Med. Chem.Lett. 2006, 16, 2229.
2. [2]
3. [3]
  (a) Li, Z. P.; Li, C. J. J. Am. Chem.Soc. 2004, 126, 11810.
  (b) Li, Z. P.; Li, C. J. Eur. J. Org. Chem. 2005, 44, 3173.
  (c) Li, Z. P.; Li, C. J. Org. Lett. 2004, 6, 4997.
  (d) Li, Z. P.; Li, C. J. J. Am. Chem. Soc. 2005, 127, 3672.
  (e) Baslé, O.; Li, C. J. Chem. Commun. 2009, 27, 4124.
  (f) Baslé, O.; Li, C. J. Green Chem. 2007, 9, 1047.
  (g) Baslé, O.; Borduas, N.; Dubois, P.; Chapuzet, J. M.; Chan, T. H.; Lessard, J.; Li, C. J. Chem. Eur. J. 2010, 16, 8162.
  (h) Li, Z. P.; MacLeod, P. D.; Li, C. J. Tetrahedron: Asymmetry 2006, 17, 590.
4. [4]
  (a) Liu, P.; Zhou, C. Y.; Xiang, S.; Che, C. M. Chem.Commun. 2010, 46, 2739.
  (b) Shu, X. Z.; Xia, X. F.; Yang, Y. F.; Ji, K. G.; Liu, X. Y.; Liang, Y. M. J.Org. Chem. 2009, 74, 7464.
  (c) Alagiri, K.; Kumara, G. S. R.; Prabhu, K. R. Chem. Commun. 2011, 47, 11787.
  (d) Sonobe, T.; Oisaki, K.; Kanai, M. Chem. Sci. 2012, 3, 3249.
  (e) Ghobrial, M.; Schnürch, M.; Mihovilovic, M. D. J. Org. Chem.2011, 76, 8781.
  (f). Volla, C. M. R.; Vogel, P. Org. Lett. 2009, 11, 1701.
5. [5]
  For recent selected examples, see:
  (a) Boess, E.; Schmitz, C.; Klussmann, M. J. Am. Chem. Soc.2012, 134, 5317.
  (b) Zhang, W.; Yang, S. P.; Shen, Z. M. Adv. Synth. Catal.2016, 358, 2392.
  (c) Wang, T.; Schrempp, M.; Berndhäuser, A.; Schiemann, O.; Menche, D. Org.Lett. 2015, 17, 3982.
  (d) Zhang, G.; Ma, Y. X.; Wang, S. L.; Zhang, Y. H.; Wang, R. J. Am.Chem. Soc. 2012, 134, 12334.
  (e) Li, Z. P.; Bohle, D. S.; Li, C. J. Proc. Natl. Acad. Sci.2006, 103, 8928.
  (f) Liu, Y. X.; Wang, C.; Xue, D.; Xiao, M.; Li, C. Q.; Xiao, J. L. Chem.-Eur.J. 2017, 23, 3051.
6. [6]
  (a) Brzozowski, M.; Forni, J. A.; Savage, G. P.; Polyzos, A. Chem. Commun. 2015, 51, 334.
  (b) Ratnikov, M. O.; Xu, X. F.; Doyle, M. P. J. Am. Chem. Soc.2013, 135, 9475.
  (c) Huang, T. Y.; Liu, X. H.; Lang, J. W.; Xu, J.; Lin, L. L.; Feng, X. M. ACS Catal. 2017, 135, 5654.
7. [7]
8. [8]
  Xie, J.; Li, H. M.; Zhou, J. C.; Cheng, Y. X.; Zhu, C. J. Angew. Chem., Int. Ed. 2012, 51, 1252.
9. [9]
  Ratnikov, M. O.; Doyle, M. P. J. Am.Chem. Soc. 2013, 135, 1549.
10. [10]
  Patil, M. R.; Dedhia, N. P.; Kapdi, A. R.; Vijay Kumar, A. J.Org. Chem. 2018, 83, 4477.
11. [11]
12. [12]
  Zhou, S. B.; Wang, J.; Lin, D. Z.; Zhao, F.; Liu, H. J. Org.Chem. 2013, 78, 11204.
13. [13]
  Kumar, P.; Sharma, A. K.; Singh, R.; Guntreddi, T. W.; Singh, K. N. Adv.Synth. Catal. 2018, 360, 1786.
14. [14]
  (a) Jin, L. K; Wan, L.; Feng, J.; Cai, C. Org. Lett. 2015, 17, 4726.
  (b) Li, Z. L.; Sun, K. K.; Cai, C. Org. Lett. 2018, 20, 6420.
15. [15]
  Li, Z. L.; Wu, P. Y.; Sun, K. K.; Cai, C. New J. Chem.2019, 43, 12152.
16. [16]
  Whittaker, A. M.; Dong, V. M. Angew. Chem., Int.Ed. 2015, 54, 1312.
17. [17]
  Wang, X.; Xie, P. P.; Qiu, R. H.; Zhu, L. Z.; Liu, T.; Li, Y.; Iwasaki, T.; Au, C. T.; Xu, X. H.; Xia, Y. Z.; Yin, S. F.; Kambe, N. Chem. Commun.2017, 53, 8316.
18. [18]
  Kawasaki, T.; Ishida, N.; Murakami, M. J. Am. Chem.Soc. 2020, 142, 3366.
19. [19]
  Verheyen, T.; van Turnhout, L.; Vandavasi, J. K.; Isbrandt, E. S.; De Borggraeve, W. M.; Newman, S. G. J. Am. Chem. Soc. 2019, 141, 6869.
20. [20]
  Zhong, J. J.; Meng, Q. Y.; Wang, G. X.; Liu, Q.; Chen, B.; Feng, K.; Tung, C. H.; Wu, L. Z. Chem. Eur. J. 2013, 19, 6443.
21. [21]
  Shi, L.; Wang, M.; Fan, C. A.; Zhang, F. M.; Tu, Y. Q. Org. Lett.2003, 5, 3515.
22. [22]
  Jiang, J. X.; Li, Y. Y.; Wu, X. F.; Xiao, J. L.; Adams, D. J.; Cooper, A. I. Macromolecules 2013, 46, 8779.
23. [23]
  Liu, Q.; Li, Y. N.; Zhang, H. H.; Chen, B.; Tung, C. H.; Wu, L. Z. Chem.-Eur.J. 2012, 18, 620.
24. [24]
  Sharma, K.; Borah, A.; Neog, K.; Gogoi, P. ChemistrySelect 2016, 1, 4620.
25. [25]
  Cherevatskaya, M.; Neumann, M.; Füldner, S.; Harlander, C.; Kümmel, S.; Dankesreiter, S.; Pfitzner, A.; Zeitler, K.; König, B. Angew. Chem., Int. Ed. 2012, 51, 4062.
26. [26]
  Periasamy, M.; Shanmugaraja, M.; Reddy, P. O.; Ramusagar, M.; Rao, G. A. J. Org. Chem. 2017, 82, 4944.
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