Chemo-selective couplings of anilines and acroleins/enones under substrate control and condition control

doi:10.1016/S1872-2067(18)63134-1

Abstract

Abstract:

Rh(Ⅲ)-catalyzed C-H activation of N-protected anilines and chemo-divergent couplings with acroleins/enones have been realized for synthesis of three classes of heterocycles. The oxidative coupling of N-pyridylaniline afforded dihydroquinolones with the acrolein being a major hydrogen acceptor. When the directing group was replaced by pyrimidyl in the same system, redox-neutral coupling occurred to afford hemiaminal ethers. Oxidative annulation of N-pyridylanilines with enones using AgBF₄ oxidant afforded atropisomeric quinolinium salts.

Key words: Rh(III)-catalysis, Chemo-selectivity, Annulation, Substrate control, Condition control

Xukai Zhou, Jiaqiong Sun, Xingwei Li. Chemo-selective couplings of anilines and acroleins/enones under substrate control and condition control[J]. Chinese Journal of Catalysis, 2018, 39(11): 1782-1791.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(18)63134-1

https://www.cjcatal.com/EN/Y2018/V39/I11/1782

References

[1] J. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res., 2008, 41, 1013-1025.
[2] L. Ackermann, Chem. Rev., 2011, 111, 1315-1345.
[3] D. Y. K. Chen, S. W. Youn, Chem. Eur. J., 2012, 18, 9452-9474.
[4] R. Y. Zhu, M. E. Farmer, Y. Q. Chen, J. Q. Yu, Angew. Chem. Int. Ed., 2016, 55, 10578-10599.
[5] T. Gensch, M. N. Hopkinson, F. Glorius, J. Wencel-Delord, Chem. Soc. Rev., 2016, 45, 2900-2936.
[6] Y. Wei, P. Hu, M. Zhang, W. P. Su, Chem. Rev., 2017, 117, 8864-8907.
[7] Y. Park, Y. Kim, S. Chang, Chem. Rev., 2017, 117, 9247-9301.
[8] C. G. Newton, S. G. Wang, C. C. Oliveira, N. Cramer, Chem. Rev., 2017, 117, 8908-8976.
[9] J. R. Hummel, J. A. Boerth, A. J. Ellman, Chem. Rev., 2017, 117, 9163-9227.
[10] Y. D. Yang, J. B. Lan, J. S. You, Chem. Rev., 2017, 117, 8787-8863.
[11] T. Piou, T. Rovis, Acc. Chem. Res., 2018, 51, 170-180.
[12] S. R. Neufeldt, M. S. Sanford, Acc. Chem. Res., 2012, 45, 936-946.
[13] J. J. Mousseau, A. B. Charette, Acc. Chem. Res., 2013, 46, 412-424.
[14] T. Iwai, M. Sawamura, ACS. Catal., 2015, 5, 5031-5040.
[15] J. Park, S. Chang, Chem. Asian J., 2018, 13, 1089-1102.
[16] O. Eisenstein, J. Milani, R. N. Perutz, Chem. Rev., 2017, 117, 8710-8753.
[17] T. Yoshino, S. Matsunaga, Adv. Synth. Catal., 2017, 359, 1245-1262.
[18] D. Vidal, G. Olivo, M. Costas, Chem. Eur. J., 2018, 24, 5042-5054.
[19] X. C. Cambeiro, T. C. Boorman, P. F. Lu, I. Larrosa, Angew. Chem. Int. Ed., 2013, 52, 1781-1784.
[20] C. Huang, J. Wu, C. J. Song, R. Ding, Y. Qiao, H. W. Hou, J. B. Chang, Y. T. Fan, Chem. Commun., 2015, 51, 10353-10356.
[21] K. H. He, W. D. Zhang, M. Y. Yang, K. L. Tang, M. N. Qu, Y. S. Ding, Y. Li, Org. Lett., 2016, 18, 2840-2843.
[22] S. Hammes-Schiffer, ChemPhysChem, 2002, 3, 33-42.
[23] R. H. D. Lyngdoh, H. F. Schaefer Ⅲ, Acc. Chem. Res., 2009, 42, 563-572.
[24] L. Wang, J. Xiao, Top. Curr. Chem., 2016, 374, 17-71.
[25] D. B. Rice, A. A. Massie, T. A. Jackson, Acc. Chem. Res., 2017, 50, 2706-2717.
[26] T. Satoh, M. Miura, Chem. Eur. J., 2010, 16, 11212-11222.
[27] G. Y. Song, X. W. Li, Acc. Chem. Res., 2015, 48, 1007-1020.
[28] Y. D. Yang, K. Z. Li, Y. Y. Cheng, D. Y. Wan, M. L. Li, J. S. You, Chem. Commun., 2016, 52, 2872-2884.
[29] P. Gandeepan, C. H. Cheng, Chem. Asian. J., 2016, 11, 448-460.
[30] M. Gulias, J. L. Mascarenas, Angew. Chem. Int. Ed., 2016, 55, 11000-11019.
[31] X. F. Wu, Transition Metal-Catalyzed Heterocycle Synthesis via C-H Activation, Wiley-VCH:Weinheim, 2016.
[32] Y. W. Xu, F. Wang, S. J. Yu, X. W. Li, Chin. J. Catal., 2017, 38, 1390-1398.
[33] X. K. Zhou, S. J. Yu, Z. S. Qi, X. W. Li, Sci. China. Chem., 2015, 58, 1297-1301.
[34] J. L. Chen, G. Y. Song, C. L. Pan, X. W. Li, Org. Lett., 2010, 12, 5426-5429.
[35] J. T. Xia, X. F. Yang, Y. Y. Li, X. W. Li, Org. Lett., 2017, 19, 3243-3246.
[36] G. D. Tang, C. L. Pan, X. W. Li, Org. Chem. Front., 2016, 3, 87-90.
[37] F. X. Zhu, Y. H. Li, Z. C. Wang, X. F. Wu, Adv. Synth. Catal., 2016, 358, 3350-3354.
[38] X. K. Zhou, J. T. Xia, G. F. Zheng, L. H. Kong, X. W. Li, Angew. Chem. Int. Ed., 2018, 57, 6681-6685.
[39] Z. Mazloomi, R. Pretorius, O. Pàmies, M. Albrecht, M. Diéguez, Inorg. Chem., 2017, 56, 11282-11298.
[40] K. M. Waldie, K. R. Flajslik, E. McLoughlin, C. E. D. Chidsey, R. M. Waymouth, J. Am. Chem. Soc., 2017, 139, 738-748.
[41] F. Saleem, G. K. Rao, A. Kumar, G. Mukherjee, A. K. Singh, Organometallics, 2014, 33, 2341-2351.
[42] K. I. Fujita, Y. Takahashi, M. Owaki, K. Yamamoto, R. Yamaguchi, Org. Lett., 2004, 6, 2785-2788.
[43] S. Sharma, E. Park, J. Park, I. S. Kim, Org. Lett., 2012, 14, 906-909.
[44] Z. J. Wu, K. L. Huang, Z. Z. Huang, Org. Biomol. Chem., 2017, 15, 4978-4983.
[45] M. Albrecht, R. H. Crabtree, J. Mata, E. Peris, Chem. Commun., 2002, 32-33.
[46] X. M. Huang, S. G. Xu, Q. T. Tan, M. C. Gao, M. J. Li, B. Xu, Chem. Commun., 2014, 50, 1465-1468.
[47] N. K. Mishra, M. Choi, H. Jo, Y. Oh, S. Sharma, S. H. Han, T. Jeong, S. Han, S. Y. Lee, I. S. Kim, Chem. Commun., 2015, 51, 17229-17232.
[48] S. Chanthamath, S. Takaki, K. Shibatomi, S. Iwasa, Angew. Chem. Int. Ed., 2013, 52, 5818-5821.
[49] J. P. Michael, Nat. Prod. Rep., 2007, 24, 191-222.
[50] J. P. Michael, Nat. Prod. Rep., 2008, 25, 139-165.
[51] L. Y. Wei, A. Brossi, S. L. Morris-Natschke, K. F. Bastow, K. H. Lee, Stud. Nat. Prod. Chem., 2008, 34, 3.
[52] J. P. Michael, The Alkaloids Chemistry Biology, 2016, 75, 1-498.
[53] C. Z. Luo, P. Gandeepan, Y. C. Wu, C. H. Tsai, C. H. Cheng, ACS Catal., 2015, 5, 4837-4841.
[54] P. Gandeepan, C. H. Cheng, Chem. Asian J., 2016, 11, 448-460.
[55] J. Jayakumar, C. H. Cheng, Chem. Eur. J., 2016, 22, 1800-1804.
[56] N. S. Upadhyay, J. Jayakumar, C. H. Cheng, Chem. Commun., 2017, 53, 2491-2494.
[57] W. C. Chen, P. Gandeepan, C. H. Tsai, C. Z. Luo, P. Rajamalli, C. H. Cheng, RSC Adv., 2016, 6, 63390-63397.
[58] Z. Z. Shi, C. Grohmann, F. Glorius, Angew. Chem. Int. Ed., 2013, 52, 5393-5397.
[59] P. P. Duan, X. Lan, Y. Chen, S. S. Qian, J. J. Li, L. Lu, Y. B. Lu, B. Chen, M. Hong, J. Zhao, Chem. Commun., 2014, 50, 12135-12138.
[60] J. A. Boerth, J. A. Ellman, Chem. Sci., 2016, 7, 1474-1479.
[61] A. B. Weinstein, J. A. Ellman, Org. Lett., 2016, 18, 3294-3297.
[62] T. J. Potter, J. A. Ellman, Org. Lett., 2016, 18, 3838-3841.
[63] B. X. Liu, P. J. Hu, Y. Zhang, Y. Y. Li, D. C. Bai, X. W. Li, Org. Lett., 2017, 19, 5402-5405.
[64] X. W. Li, P. Chen, J. W. Faller, R. H. Crabtree, Organometallics, 2005, 24, 4810-4815.
[65] D. C. Leitch, J. A. Labinger, J. E. Bercaw, Organometallics, 2014, 33, 3353-3365.
[66] M. Morimoto, T. Miura, M. Murakami, Angew. Chem. Int. Ed., 2015, 54, 12659-12663.
[67] W. H. Li, L. Wu, S. S. Li, C. F. Liu, G. T. Zhang, L. Dong, Chem. Eur. J., 2016, 22, 17926-17929.
[68] N. N. Lü, Y. Liu, C. H. Xiong, Z. X. Liu, Y. H. Zhang, Org. Lett., 2017, 19, 4640-4643.
[69] H. Steinhagen, E. J. Corey, Angew. Chem. Int. Ed., 1999, 38, 1928-1931.
[70] C. L. Mathis, B. M. Gist, C. K. Frederickson, K. M. Midkiff, C. C. Marvin, Tetrahedron Lett., 2013, 54, 2101-2104.
[71] M. L. Deb, S. S. Dey, I. Bento, M. T. Barros, C. D. Maycock, Angew. Chem. Int. Ed., 2013, 52, 9791-9795.
[72] A. Modak, U. Dutta, R. Kancherla, S. Maity, M. Bhadra, S. M. Mobin, D. Maiti, Org. Lett., 2014, 16, 2602-2605.
[73] K. L. Chen, B. Gao, Y. G. Shang, J. Y. Du, Q. L. Gu, J. X. Wang, Org. Biomol. Chem., 2017, 15, 8770-8779.
[74] P. Bai, Y. Q. Li, Z. Z. Huang, Org. Lett., 2017, 19, 1374-1377.
[75] J. Kim, S. W. Park, M. H. Baik, S. Chang, J. Am. Chem. Soc., 2015, 137, 13448-13451.
[76] P. Gandeepan, C. H. Cheng, Chem. Asian J., 2016, 18, 448-460.