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

doi:10.6023/cjoc202004028

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 2099-2107.DOI: 10.6023/cjoc202004028 Previous Articles Next Articles

镍催化分子氧氧化脱氢偶联反应制备N-芳基四氢异喹啉化合物

王慧, 王安玮, 夏珍珍, 周维友, 孙中华, 钱俊峰, 何明阳

常州大学石油化工学院江苏省绿色催化材料与技术重点实验室江苏常州 213164

收稿日期:2020-04-18 修回日期:2020-05-04 发布日期:2020-05-15
通讯作者: 周维友 E-mail:zhouwy426@126.com
基金资助:
江苏省绿色催化材料与技术重点实验室基金（No.BM2012110）、江苏省研究生科研与实践创新计划（No.KYCX19_1746）、江苏省自然科学基金（No.BK20181461）资助项目.

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

Wang Hui, Wang Anwei, Xia Zhenzhen, Zhou Weiyou, Sun Zhonghua, Qian Junfeng, He Mingyang

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

Received:2020-04-18 Revised:2020-05-04 Published:2020-05-15
Supported by:
Project 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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Abstract

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.

Key words: cross-dehydrogenative coupling, C-H activation, nickel, molecular oxygen, N-aryl tetrahydroisoquinoline

Cite this article

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.

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[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] (a) Anastas, P.; Eghbali, N. Chem. Soc. Rev. 2010, 39, 301.
(b) Li, Z.; Li, C. J. J. Am. Chem. Soc. 2005, 127, 6968.
(c) Wang, G.; Wang, J. T.; Zhao, B.; Chen, H.; Zhang, P. K.; Han, S. L. Tetrahedron Lett. 2020, 61, 151426.
(d) Zhang, X. L.; Pan, G. F.; Zhu, X. Q.; Guo, R. L.; Gao, Y. R.; Wang, Y. Q. Org. Lett. 2019, 21, 2731.
(e) Wang, D. Y.; Guo, S. H.; Pan, G. L.; Zhu, X. Q.; Gao, Y. R.; Wang, Y. Q. Org. Lett. 2018, 20, 1794.
(f) Sun, Y. L.; Xu, W. X.; Ye, F. X.; Weng, J. Q. Chin. J. Org. Chem. 2019, 39, 3065(in Chinese). (孔瑶蕾, 徐雯秀, 叶飞霞, 翁建全, 有机化学, 2019, 39, 3065.)
(f) Tang, H.; Luo, J. F.; Xie, P. Chin. J. Org. Chem. 2019, 39, 2735(in Chinese). (唐灏, 骆钧飞, 解攀, 有机化学, 2019, 39, 2735.)
[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] (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] 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] (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] (a) Wang, M. Z.; Zhou, C. Y.; Wong, M. K.; Che, C. M. Chem.-Eur. J. 2010, 16, 5723.
(b) Yu, A. H.; Gu, Z.; Chen, D.; He, W. M.; Tan, P.; Xiang, J. N. Catal. Commun. 2009, 11, 162.
(c) Zeng, M.; Song, C.; Cui, D. M. Chin. J. Org. Chem. 2017, 37, 1352(in Chinese). (曾明, 宋婵, 崔冬梅, 有机化学, 2017, 37, 1352.)
(d) Rana, P.; Gaur, R.; Gupta, R.; Arora, G.; Jayashree, A.; Sharma R. K. Chem. Commun. 2019, 55, 7402.
[8] Xie, J.; Li, H. M.; Zhou, J. C.; Cheng, Y. X.; Zhu, C. J. Angew. Chem., Int. Ed. 2012, 51, 1252.
[9] Ratnikov, M. O.; Doyle, M. P. J. Am. Chem. Soc. 2013, 135, 1549.
[10] Patil, M. R.; Dedhia, N. P.; Kapdi, A. R.; Vijay Kumar, A. J. Org. Chem. 2018, 83, 4477.
[11] For recent selected examples, see: (a) Ueda, H.; Yoshida, K.; Tokuyama, H. Org. Lett. 2014, 16, 4194.
(b) Alagiri, K.; Devadig, P.; Prabhu, K. R. Chem.-Eur. J. 2012, 18, 5160.
(c) Kumar, R. A.; Saidulu, G.; Prasad, K. R.; Kumar, G. S.; Sridhar, B.; Reddy, K. R. Adv. Synth. Catal. 2012, 354, 2985.
(d) Xiao, Y. X.; Liu, Z. Q. Acta Chim. Sinica 2019, 77, 874(in Chinese). (肖莹霞, 柳忠全, 化学学报, 2019, 77, 874.)
(e) Guan, H. H.; Chen, L.; Liu, L. Acta Chim. Sinica 2018, 76, 440(in Chinese). (关弘浩, 陈磊, 刘磊, 化学学报, 2018, 76, 440.)
(f) Pan, X. H.; Liu, X. G.; Sun, S. T.; Meng, Z. L.; Liu, L. Chin. J. Chem. 2018, 36, 1187.
[12] Zhou, S. B.; Wang, J.; Lin, D. Z.; Zhao, F.; Liu, H. J. Org. Chem. 2013, 78, 11204.
[13] Kumar, P.; Sharma, A. K.; Singh, R.; Guntreddi, T. W.; Singh, K. N. Adv. Synth. Catal. 2018, 360, 1786.
[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] Li, Z. L.; Wu, P. Y.; Sun, K. K.; Cai, C. New J. Chem. 2019, 43, 12152.
[16] Whittaker, A. M.; Dong, V. M. Angew. Chem., Int. Ed. 2015, 54, 1312.
[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] Kawasaki, T.; Ishida, N.; Murakami, M. J. Am. Chem. Soc. 2020, 142, 3366.
[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] 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] Shi, L.; Wang, M.; Fan, C. A.; Zhang, F. M.; Tu, Y. Q. Org. Lett. 2003, 5, 3515.
[22] Jiang, J. X.; Li, Y. Y.; Wu, X. F.; Xiao, J. L.; Adams, D. J.; Cooper, A. I. Macromolecules 2013, 46, 8779.
[23] Liu, Q.; Li, Y. N.; Zhang, H. H.; Chen, B.; Tung, C. H.; Wu, L. Z. Chem.-Eur. J. 2012, 18, 620.
[24] Sharma, K.; Borah, A.; Neog, K.; Gogoi, P. ChemistrySelect 2016, 1, 4620.
[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] Periasamy, M.; Shanmugaraja, M.; Reddy, P. O.; Ramusagar, M.; Rao, G. A. J. Org. Chem. 2017, 82, 4944.

镍催化分子氧氧化脱氢偶联反应制备N-芳基四氢异喹啉化合物

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

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