Co(III)/Zn(II)-catalyzed dearomatization of indoles and coupling with carbenes from ene-yne ketones via intramolecular cyclopropanation

doi:10.1016/S1872-2067(18)63154-7

Abstract

Abstract:

A straightforward and efficient protocol for dearomatizing indoles is described. The reaction, catalyzed by an inexpensive Co(Ⅲ)/Zn(Ⅱ) catalyst, starts from easily accessible N-pyrimidinyl indoles and ene-yne ketones. Mild reaction conditions, high diastereoselectivity, a broad substrate scope, effective functional group tolerance, and reasonable to remarkable yields were observed.

Key words: Co(III)/Zn(II) catalysis, Dearomatization, Cyclopropanation, Carbene, Indole

Na Li, Junbiao Chang, Lingheng Kong, Shuangjing Wang, Dandan Wang, Miao Cheng, Xingwei Li. Co(III)/Zn(II)-catalyzed dearomatization of indoles and coupling with carbenes from ene-yne ketones via intramolecular cyclopropanation[J]. Chinese Journal of Catalysis, 2018, 39(12): 1881-1889.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(18)63154-7

https://www.cjcatal.com/EN/Y2018/V39/I12/1881

References

[1] D. Jin, F. Zhang, D. C. Zhang, Chin. J. Org. Chem., 2010, 30, 1005-1009.
[2] D. Y. Liu, G. W. Zhao, L. Xiang, Eur. J. Org. Chem., 2010, 2010, 3975-3984.
[3] S. Anas, H. B. Kagan, Tetrahedron:Asymmetry, 2009, 20, 2193-2199.
[4] J. Bonjoch, D. Solé, S. García-Rubio, J. Bosch, J. Am. Chem. Soc., 1997, 119, 7230-7240.
[5] D. Zhang, H. Song, Y. Qin, Acc. Chem. Res., 2011, 44, 447-457.
[6] X. Deng, K. J. Liang, X. G. Tong, M. Ding, D. S. Li, C. F. Xia, Org. Lett., 2014, 16, 3276-3279.
[7] T. Wang, Q. G. Xu, P. Yu, X. X. Liu, J. M. Cook, Org. Lett., 2001, 3, 345-348.
[8] X. Y. Fu, J. M. Cook, J. Am. Chem. Soc., 1992, 114, 6910-6912.
[9] J. Li, T. Wang, P. Yu, A. Peterson, R. Weber, D. Soerens, D. Grubisha, D. Bennett, J. M. Cook, J. Am. Chem. Soc., 1999, 121, 6998-7010.
[10] S. J. Jin, J. Gong, Y. Qin, Angew. Chem. Int. Ed., 2015, 54, 2228-2231.
[11] H. X. Huang, S. J. Jin, J. Gong, D. Zhang, H. Song, Y. Qin, Chem. Eur. J., 2015, 21, 13284-13290.
[12] M. S. Kirillova, M. E. Muratore, R. Dorel, A. M. Echavarren, J. Am. Chem. Soc., 2016, 138, 3671-3674.
[13] L. A. Paquette, Chem. Rev., 1986, 86, 733-750.
[14] H. N. C. Wong, M. Y. Hon, C. W. Tse, Y. C. Yip, J. Tanko, T. Hudlicky, Chem. Rev., 1989, 89, 165-198.
[15] O. G. Kulinkovich, Pol. J. Chem., 1997, 71, 849-882.
[16] A. de Meijere, S. I. Kozhushkov, L. P. Hadjiarapoglou, Top. Curr. Chem., 2000, 207, 149-227.
[17] H. Lebel, J. F. Marcoux, C. Molinaro, A. B. Charetter, Chem. Rev., 2003, 103, 977-1050.
[18] D. Gagnon, C. Spino, J. Org. Chem., 2009, 74, 6035-6041.
[19] H. Song, J. Yang, W. Chen, Y. Qin, Org. Lett., 2006, 8, 6011-6014.
[20] B. He, H. Song, Y. Du, Y. Qin, J. Org. Chem., 2009, 74, 298-304
[21] A. R. Reddy, F. Hao, K. Wu, C. Y. Zhou, C. M. Che, Angew. Chem. Int. Ed., 2016, 55, 1810-1815.
[22] B. Zhang, A. G. H. Wee, Chem. Commun., 2008, 4837-4839.
[23] B. Zhang, A. G. H. Wee, Org. Biomol. Chem., 2012, 10, 4597-4608.
[24] G. Özüduru, T. Schubach, M. M. K. Boysen, Org. Lett., 2012, 14, 4990-4993.
[25] D. Gagnon, C. Spino, J. Org. Chem., 2009, 74, 6035-6041.
[26] W. J. Welstead Jr, H. F. Stauffer Jr, L. F. Sancilio, J. Med. Chem., 1974, 17, 544-547.
[27] E. Wenkert, M. E. Alonso, H. E. Gottlieb, E. L. Sanchez, R. Pellicciari, P. Cogolli, J. Org. Chem., 1977, 42, 3945-3949.
[28] H. Keller, E. Langer, H. Lehner, Monatsh. Chem., 1977, 108, 123-131.
[29] F. Gnad, M. Poleschak, O. Reiser, Tetrahedron Lett., 2004, 45, 4277-4280.
[30] X. J. Zhang, S. P. Liu, M. Yan, Chin. J. Chem., 2008, 26, 716-720.
[31] D. Zhang, H. Song, Y. Qin, Acc. Chem. Res., 2011, 44, 447-457.
[32] H. M. L. Davies, J. E. Spangler, Adv. Heterocycl. Chem., 2013, 110, 43-72.
[33] H. M. L. Davies, S. J. Hedley, Chem. Soc. Rev., 2007, 36, 1109-1119.
[34] H. Xu, Y. P. Li, Y. Cai, G. P. Wang, S. F. Zhu, Q. L. Zhou, J. Am. Chem. Soc., 2017, 139, 7697-7700.
[35] W. T. Wu, L. Zhang, S. L. You, Acta Chim. Sinica., 2017, 75, 419-438.
[36] D. C. Wang, M. S. Xie, H. M. Guo, G. R. Qu, M. C. Zhang, S. L. You, Angew. Chem. Int. Ed., 2016, 55, 14111-14115.
[37] W. Du, Q. S. Gu, Z. L. Li, D. Yang, J. Am. Chem. Soc., 2015, 137, 1130-1135.
[38] Y. Y. Zhou, C. Uyeda, Angew. Chem. Int. Ed., 2016, 55, 3171-3175.
[39] H. Rudler, T. Durand-Réville, J. Organomet. Chem., 2001, 617-618, 571-587.
[40] D. Dhanaka, R. Kurodab, C. B. Reese, Tetrahedron Lett., 1987, 28, 1827-1830.
[41] H. E. Simmons, R. D. Smith, J. Am. Chem. Soc., 1958, 80, 5323-5324.
[42] S. R. Goudreau, A. B. Charette, J. Am. Chem. Soc., 2009, 131, 15633-15635.
[43] K. Miki, T. Yokoi, F. Nishino, K. Ohe, S. Uemura, J. Organomet. Chem., 2002, 645, 228-234.
[44] K. Miki, F. Nishino, K. Ohe, S. Uemura, J. Am. Chem. Soc., 2002, 124, 5260-5261.
[45] K. Miki, T. Yokoi, F. Nishino, Y. Kato, Y. Washitake, K. Ohe, S. Uemura, J. Org. Chem., 2004, 69, 1557-1564.
[46] K. Miki, S. Uemura, K. Ohe, Chem. Lett., 2005, 34, 1068-1072.
[47] R. Vicente, J. Gonzalez, L. Riesgo, J. Gonzalez, L. A. Lopez, Angew. Chem. Int. Ed., 2012, 51, 8063-8067.
[48] C. X. Zhuo, W. Zhang, S. L.You, Angew. Chem. Int. Ed., 2012, 51, 12662-12686.
[49] W. Chen, D. S. Ji, Y. C Luo, Z. Y. Wang, P. F. Xu, Org. Chem. Front., 2018, 5, 1768-1771.
[50] N. Yoshikai, ChemCatChem., 2015, 7, 732-734.
[51] M. Moselage, J. Li, L. Ackermann, ACS Catal., 2016, 6, 498-525.
[52] X. L. Han, C. J. Zhou, X. G. Liu, S. S. Zhang, H. G. Wang, Q. J. Li, Org. Lett., 2017, 19, 6108-6111.
[53] W. Zhang, F. Han, J. Tong, C. Xia, J. Liu, Chin. J. Catal., 2017, 38, 805-812.
[54] F. Wang, Q. Wang, M. Bao, X. W. Li, Chin. J. Catal., 2016, 37, 1423-1430.
[55] Y. Chen, J. V. Ruppol, X. P. Zhang, J. Am. Chem. Soc., 2007, 129, 12074-12075.
[56] W. J. Kerr, D. M. Lindsay, P. K. Owens, M. Reid, T. Tuttle, S. Campos, ACS Catal., 2017, 7, 7182-7186.
[57] L. Ackermann, A.V. Lygin, Org. Lett., 2011, 13, 3332-3335.
[58] M. Nishino, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int. Ed., 2012, 51, 6993-6997.
[59] N. Li, J. B. Chang, L. H. Kong, X. W. Li, Org. Chem. Front., 2018, 5, 1978-1982.