Cobalt-catalyzed redox-neutral synthesis of isoquinolines: C-H activation assisted by an oxidizing N-S bond

doi:10.1016/S1872-2067(16)62491-9

Chinese Journal of Catalysis ›› 2016, Vol. 37 ›› Issue (8): 1423-1430.DOI: 10.1016/S1872-2067(16)62491-9

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Cobalt-catalyzed redox-neutral synthesis of isoquinolines: C-H activation assisted by an oxidizing N-S bond

Fen Wang^a,b, Qiang Wang^b, Ming Bao^a, Xingwei Li^b

a. School of Chemistry and Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning, China;
b. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China

Received:2016-06-06 Revised:2016-06-24 Online:2016-07-29 Published:2016-08-01
Contact: Xingwei Li
Supported by:
This work was supported by the Dalian Institute of Chemical Physics, Chinese Academy of Sciences and the National Natural Science Foundation of China (21272231).

Abstract

Fen Wang, Qiang Wang, Ming Bao, Xingwei Li . Cobalt-catalyzed redox-neutral synthesis of isoquinolines: C-H activation assisted by an oxidizing N-S bond[J]. Chinese Journal of Catalysis, 2016, 37(8): 1423-1430.

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References

[1] K. R. Roesch, R. C. Larock, J. Org. Chem., 1998, 63, 5306-5307.
[2] K. R. Roesch, R. C. Larock, Org. Lett., 1999, 1, 553-556.
[3] K. R. Roesch, H. M. Zhang, R. C. Larock, J. Org. Chem., 2001, 66, 8042-8051.
[4] G. X. Dai, R. C. Larock, Org. Lett., 2002, 4, 193-196.
[5] G. X. Dai, R. C. Larock, J. Org. Chem., 2003, 68, 920-928.
[6] N. Todorovic, E. Awuah, S. Albu, C. Ozimok, A. Capretta, Org. Lett., 2011, 13, 6180-6183.
[7] L. Florentino, F. Aznar, C. Valdés, Org. Lett., 2012, 14, 2323-2325.
[8] T. Satoh, M. Miura, Chem. Eur. J., 2010, 16, 11212-11222.
[9] F. W. Patureau, J. Wencel-Delord, F. Glorius, Aldrichim. Acta, 2012, 45, 31-41.
[10] G. Y. Song, F. Wang, X. W. Li, Chem. Soc. Rev., 2012, 41, 3651-3678.
[11] G. Y. Song, X. W. Li, Acc. Chem. Res., 2015, 48, 1007-1020.
[12] N. Kuhl, N. Schrçder, F. Glorius, Adv. Synth. Catal., 2014, 356, 1443-1460.
[13] B. H. Ye, N. Cramer, Acc. Chem. Res., 2015, 48, 1308-1318.
[14] S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, C. H. Jun, Org. Lett., 2003, 5, 2759-2761.
[15] N. Guimond, K. Fagnou, J. Am. Chem. Soc., 2009, 131, 12050-12051.
[16] K. Parthasarathy, C. H. Cheng, J. Org. Chem., 2009, 74, 9359-9364.
[17] T. Fukutani, N. Umeda, K. Hirano, T. Satoh, M. Miura, Chem. Commun., 2009, 5141-5143.
[18] P. C. Too, Y. F. Wang, S. Chiba, Org. Lett., 2010, 12, 5688-5691.
[19] L. H. Kong, F. Xie, S. J. Yu, Z. S. Qi, X. W. Li, Chin. J. Catal., 2015, 36, 925-932.
[20] T. K. Hyster, T. Rovis, Chem. Commun., 2011, 47, 11846-11848.
[21] P. C. Too, S. H. Chua, S. H. Wong, S. Chiba, J. Org. Chem., 2011, 76, 6159-6168.
[22] X. H. Wei, M. Zhao, Z. Y. Du, X. W. Li, Org. Lett., 2011, 13, 4636-4639.
[23] Y. F. Wang, K. K. Toh, J. Y. Lee, S. Chiba, Angew. Chem. Int. Ed., 2011, 50, 5927-5931.
[24] K. Morimoto, K. Hirano, T. Satoh, M. Miura, Chem. Lett., 2011, 40, 600-602.
[25] L. Y. Zheng, J. Ju, Y. H. Bin, R. M. Hua, J. Org. Chem., 2012, 77, 5794-5800.
[26] S. C. Chuang, P. Gandeepan, C. H. Cheng, Org. Lett., 2013, 15, 5750-5753.
[27] W. T. Liu, X. H. Hong, B. Xu, Synthesis, 2013, 45, 2137-2149.
[28] D. S. Kim, J. W. Park, C. H. Jun, Adv. Synth. Catal., 2013, 355, 2667-2679.
[29] D. B. Zhao, F. Lied, F. Glorius, Chem. Sci., 2014, 5, 2869-2873.
[30] J. T. Zhang, H. S. Qian, Z. X. Liu, C. H. Xiong, Y. H. Zhang, Eur. J. Org. Chem., 2014, 8110-8118.
[31] X. C. Huang, X. H. Yang, R. J. Song, J. H. Li, J. Org. Chem., 2014, 79, 1025-1031.
[32] W. J. Han, G. Y. Zhang, G. X. Li, H. M. Huang, Org. Lett., 2014, 16, 3532-3535.
[33] C. Kornhaaß, J. Li, L. Ackermann, J. Org. Chem., 2012, 77, 9190-9198.
[34] R. K. Chinnagolla, S. Pimparkar, M. Jeganmohan, Org. Lett., 2012, 14, 3032-3035.
[35] R. K. Chinnagolla, S. Pimparkar, M. Jeganmohan, Chem. Commun., 2013, 49, 3703-3705.
[36] P. Villuendas, E. P. Urriolabeitia, J. Org. Chem., 2013, 78, 5254-5263.
[37] S. Gupta, J. Han, Y. Kim, S. W. Lee, Y. H. Rhee, J. Park, J. Org. Chem., 2014, 79, 9094-9103.
[38] T. Gerfaud, L. Neuville, J. Zhu, Angew. Chem. Int. Ed., 2009, 48, 572-577.
[39] D. A. Candito, M. Lautens, Angew. Chem. Int. Ed., 2009, 48, 6713-6716.
[40] M. Blanchot, D. A. Candito, F. Larnaud, M. Lautens, Org. Lett., 2011, 13, 1486-1489.
[41] N. Guimond, C. Gouliaras, K. Fagnou, J. Am. Chem. Soc., 2010, 132, 6908-6909.
[42] T. Yoshino, H. Ikemoto, S. Matsunaga, M. Kanai, Angew. Chem. Int. Ed., 2013, 52, 2207-2211.
[43] B. Sun, T. Yoshino, M. Kanai, S. Matsunaga, Angew. Chem. Int. Ed., 2015, 54, 12968-12972.
[44] D. B. Zhao, J. H. Kim, L. Stegemann, C. A. Strassert, F. Glorius, Angew. Chem. Int. Ed., 2015, 54, 4508-4511.
[45] D. G. Yu, T. Gensch, F. de Azambuja, S. Vásquez-Céspedes, F. Glorius, J. Am. Chem. Soc., 2014, 136, 17722-17725.
[46] J. Li, L. Ackermann, Angew. Chem. Int. Ed., 2015, 54, 8551-8554.
[47] C. Kornhaaß, C. Kuper, L. Ackermann, Adv. Synth. Catal., 2014, 356, 1619-1624.
[48] A. B. Pawar, S. Chang, Org. Lett., 2015, 17, 660-663.
[49] P. Patel, S. Chang, ACS Catal., 2015, 5, 853-858.
[50] J. R. Hummel, J. A. Ellman, Org. Lett., 2015, 17, 2400-2403.
[51] J. R. Hummel, J. A. Ellman, J. Am. Chem. Soc., 2015, 137, 490-498.
[52] L. Grigorjeva, O. Daugulis, Angew. Chem. Int. Ed., 2014, 53, 10209-10212.
[53] Y. J. Liang, Y. F. Liang, C. H. Tang, Y. Z. Yuan, N. Jiao, Chem. Eur. J., 2015, 21, 16395-16399.
[54] Z. Z. Zhang, B. Liu, C. Y. Wang, B. F. Shi, Org. Lett., 2015, 17, 4094-4097.
[55] X. G. Liu, S. S. Zhang, C. Y. Jiang, J. Q. Wu, Q. J. Li, H. G. Wang, Org. Lett., 2015, 17, 5404-5407.
[56] S. S. Zhang, X. G. Liu, S. Y. Chen, D. H. Tan, C. Y. Jiang, J. Q. Wu, Q. J. Li, H. G. Wang, Adv. Synth. Catal., 2016, 358, 1705-1710.
[57] M. Sen, D. Kalsi, B. Sundararaju, Chem. Eur. J., 2015, 21, 15529-15533.
[58] F. Wang, H. Wang, Q. Wang, S. J. Yu, X. W. Li, Org. Lett., 2016, 18, 1306-1309.
[59] L. H. Kong, S. J. Yu, X. K. Zhou, X. W. Li, Org. Lett., 2016, 18, 588-591.
[60] Y. F. Wang, K. K. Toh, J. Y. Lee, S. Chiba, Angew. Chem. Int. Ed., 2011, 50, 5927-5931.
[61] S. J. Yu, S. Liu, Y. Lan, B. S. Wan, X. W. Li, J. Am. Chem. Soc., 2015, 137, 1623-1631.
[62] Q. R. Zhang, J. R. Huang, W. Zhang, L. Dong, Org. Lett., 2014, 16, 1684-1687.

Cobalt-catalyzed redox-neutral synthesis of isoquinolines: C-H activation assisted by an oxidizing N-S bond

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