Zinc phthalocyanine as an efficient catalyst for halogen-free synthesis of formamides from amines via carbon dioxide hydrosilylation under mild conditions

Abstract

Abstract:

The combination of a zinc phthalocyanine (ZnPc) catalyst and a stoichiometric amount of dimethyl formamide (DMF) provided a simple route to formamide derivatives from amines, CO₂, and hydrosilanes under mild conditions. We deduced that formation of an active zinc-hydrogen (Zn-H) species promoted hydride transfer from the hydrosilane to CO₂. The cooperative activation of the Lewis acidic ZnPc by strongly polar DMF, led to formation of activated amines and hydrosilanes, which promoted the chemical reduction of CO₂. Consequently, the binary ZnPc/DMF catalytic system showed excellent yields and superior chemoselectivity, representing a simple and sustainable pathway for the reductive transformation of CO₂ into valuable chemicals as an alternative to conventional halogen-containing process.

Key words: Carbon dioxide, Zinc phthalocyanine, Cooperative effect, N-formylation, Hydrosilanes

Rongchang Luo, Xiaowei Lin, Jing Lu, Xiantai Zhou, Hongbing Ji. Zinc phthalocyanine as an efficient catalyst for halogen-free synthesis of formamides from amines via carbon dioxide hydrosilylation under mild conditions[J]. Chinese Journal of Catalysis, 2017, 38(8): 1382-1389.

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References

[1] Q. Liu, L. P. Wu, R. Jackstell, M. Beller, Nat. Commun., 2015, 6, 5933.
[2] A. W. Kleij, M. North, A. Urakawa, ChemSusChem, 2017, 10, 1036-1038.
[3] M. Tamura, K. Ito, Y. Nakagawa, K. Tomishige, J. Catal., 2016, 343, 75-85.
[4] C. Martín, G. Fiorani, A. W. Kleij, ACS Catal., 2015, 5, 1353-1370.
[5] M. Cokoja, M. E. Wilhelm, M. H. Anthofer, W. A. Herrmann, F. E. Kühn, ChemSusChem, 2015, 8, 2436-2454.
[6] J. W. Comerford, l. D. V. Ingram, M. North, X. Wu, Green Chem., 2015, 17, 1966-1987.
[7] D. J. Darensbourg, Chem. Rev., 2007, 107, 2388-2410.
[8] W. H. Wang, Y. Himeda, J. T. Muckerman, G. F. Manbeck, E. Fujita, Chem. Rev., 2015, 115, 12936-12973.
[9] B. Yu, L. N. He, ChemSusChem, 2015, 8, 52-62.
[10] Z. Z. Yang, L. N. He, J. Gao, A. H. Liu, B. Yu, Energy Environ. Sci., 2012, 5, 6602-6639.
[11] A. Tlili, E. Blondiaux, X. Frogneux, T. Cantat, Green Chem., 2015, 17, 157-168.
[12] C. Das Neves Gomes, O. Jacquet, C. Villiers, P. Thuéry, M. Ephri-tikhine, T. Cantat, Angew. Chem. Int. Ed., 2012, 51, 187-190.
[13] K. Motokura, M. Naijo, S. Yamaguchi, A. Miyaji, T. Baba, Chem. Lett., 2015, 44, 1217-1219.
[14] D. B. Nale, B. M. Bhanage, Synlett, 2016, 27, 1413-1417.
[15] C. Fang, C. L. Lu, M. H. Liu, Y. L. Zhu, Y. Fu, B. L. Lin, ACS Catal., 2016, 6, 7876-7881.
[16] X. F. Liu, C. Qiao, X. Y. Li, L. N. He, Green Chem., 2017, 19, 1726-1731.
[17] H. Lü, Q. Xing, C. T. Yue, Z. Q. Lei, F. W. Li, Chem. Commun., 2016, 52, 6545-6548.
[18] J. Song, B. Zhou, H. Liu, C. Xie, Q. Meng, Z. Zhang, B. Han, Green Chem., 2016, 18, 3956-3961.
[19] L. D. Hao, Y. F. Zhao, B. Yu, Z. Z. Yang, H. Y. Zhang, B. X. Han, X. Gao, Z. M. Liu, ACS Catal., 2015, 5, 4989-4993.
[20] M. Hulla, F. D. Bobbink, S. Das, P. J. Dyson, ChemCatChem, 2016, 8, 3338-3342.
[21] X. F. Liu, R. Ma, C. Qiao, H. Cao, L. N. He, Chem. Eur. J., 2016, 22, 16489-16493.
[22] K. Motokura, N. Takahashi, D. Kashiwame, S. Yamaguchi, A. Miyaji, T. Baba, Catal. Sci. Technol., 2013, 3, 2392-2396.
[23] K. Motokura, N. Takahashi, A. Miyaji, Y. Sakamoto, S. Yama-guchi, T. Baba, Tetrahedron, 2014, 70, 6951-6956.
[24] S. Q. Zhang, Q. Q. Mei, H. Y. Liu, H. Z. Liu, Z. P. Zhang, B. X. Han, RSC Adv., 2016, 6, 32370-32373.
[25] O. Jacquet, C. Das Neves Gomes, M. Ephritikhine, T. Cantat, J. Am. Chem. Soc., 2012, 134, 2934-2937.
[26] Q. H. Zhou, Y. X. Li, J. Am. Chem. Soc., 2015, 137, 10182-10189.
[27] Z. Z. Yang, B. Yu, H. Y. Zhang, Y. F. Zhao, G. P. Ji, Z. M. Liu, RSC Adv., 2015, 5, 19613-19619.
[28] S. N. Riduan, J. Y. Ying, Y. G. Zhang, J. Catal., 2016, 343, 46-51.
[29] S. Das, S. Bulut, F. D. Bobbink, M. Soudani, P. J. Dyson, Chem. Com-mun., 2016, 52, 2497-2500.
[30] B. Dong, L. Y. Wang, S. Zhao, R. L. Ge, X. D. Song, Y. Wang, Y. N. Gao, Chem. Commun., 2016, 52, 7082-7085.
[31] H. Zhou, G. X. Wang, W. Z. Zhang, X. B. Lu, ACS Catal., 2015, 5, 6773-6779.
[32] C. C. Chong, R. Kinjo, Angew. Chem. Int. Ed., 2015, 127, 12116-12120.
[33] V. B. Saptal, B. M. Bhanage, ChemSusChem, 2016, 9, 1980-1985.
[34] X. F. Liu, X. Y. Li, C. Qiao, H. C. Fu, L. N. He, Angew. Chem. Int. Ed., 2017, 156, 7425-7429.
[35] X. Frogneux, O. Jacquet, T. Cantat, Catal. Sci. Technol., 2014, 4, 1529-1533.
[36] T. V. Q. Nguyen, W. J. Yoo, S. Kobayashi, Angew. Chem. Int. Ed., 2015, 54, 9209-9212.
[37] R. A. Molla, P. Bhanja, K. Ghosh, S. S. Islam, A. Bhaumik, S. M. Islam, ChemCatChem, 2017, 9, 1939-1946.
[38] R. C. Luo, X. W. Lin, Y. J. Chen, W. Y. Zhang, X. T. Zhou, H. B. Ji, ChemSusChem, 2017, 10, 1224-1232.
[39] R. C. Luo, Y. J. Chen, Q. He, X. W. Lin, Q. H. Xu, X. H. He, W. Y. Zhang, X. T. Zhou, H. B. Ji, ChemSusChem, 2017, 10, 1526-1533.
[40] W. Y. Zhang, R. C. Luo, Q. H. Xu, Y. J. Chen, X. W. Lin, X. T. Zhou, H. B. Ji, Chin. J. Catal., 2017, 38, 736-744.
[41] W. Sattler, G. Parkin, J. Am. Chem. Soc., 2012, 134, 17462-17465.
[42] M. M. Deshmukh, S. Sakaki, Inorg. Chem., 2014, 53, 8485-8493.
[43] O. Jacquet, C. Das Neves Gomes, M. Ephritikhine, T. Cantat, Chem CatChem, 2013, 5, 117-120.
[44] H. Y. Niu, L. J. Lu, R. Y. Shi, C. W. Chiang, A. W. Lei, Chem. Commun., 2017, 53, 1148-1151.
[45] Y. H. Wang, J. Zhang, J. Liu, C. F. Zhang, Z. X. Zhang, J. Xu, S. T. Xu, F. J. Wang, F. Wang, ChemSusChem, 2015, 8, 2066-2072.