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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 8: 2471 - 2480

DOI: https://doi.org/10.6023/cjoc202112034

ARTICLES

CNN-Type Binuclear Cu(I) Complexes Catalyzed Direct Carboxylation via the Fixation of CO2 at Room Temperature

  • Fei Chen ,
  • Sheng Tao ,
  • Ning Liu ,
  • Bin Dai
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  • a School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072
    b Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003
* E-mail: ;

Received date: 2021-12-26

  Revised date: 2022-04-04

  Online published: 2022-05-18

Supported by

Young and Middle-Aged Leading Scientists Program of Shihezi City(2019RC01); Open Sharing Fund for the Large-scale Instruments and Equipment of Shihezi University.

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Abstract

A type of CNN-type binuclear Cu(Ⅰ) complexes was used in the direct carboxylation of the terminal alkynes under room temperature and atmospheric CO2 with a low catalyst loading. A broad range of the terminal alkynes were tolerated, leading to the desired propiolic acids in 83%~97% yields. The method was successfully applied to continuous carboxylation and esterification of hetero arenes. The control experimental results and literature suggest that Cs2CO3 promotes the removal of terminal alkyne hydrogen atoms, and Cu(Ⅰ) complexes play an important role in the activation of terminal alkyne by the interaction between Cu(I) center and alkynyl group.

Key words： carbon dioxide; terminal alkyne; copper catalysis; carboxylation; C—H activation

Cite this article

Fei Chen , Sheng Tao , Ning Liu , Bin Dai . CNN-Type Binuclear Cu(I) Complexes Catalyzed Direct Carboxylation via the Fixation of CO2 at Room Temperature[J]. Chinese Journal of Organic Chemistry, 2022 , 42(8) : 2471 -2480 . DOI: 10.6023/cjoc202112034

References

[1]
(a) Ye, J.-H.; Ju, T.; Huang, H.; Liao, L.-L.; Yu, D.-G. Acc. Chem. Res. 2021, 54, 2518.
[1]
(b) Song, L.; Jiang, Y.-X.; Zhang, Z.; Gui, Y.-Y.; Zhou, X.-Y.; Yu, D.-G. Chem. Commun. 2020, 56, 8355.
[1]
(c) Huang, K.; Sun, C.-L.; Shi, Z.-J. Chem. Soc. Rev. 2011, 40, 2435.
[1]
(d) Zhang, Z.; Gong, L.; Zhou, X.-Y.; Yan, S.-S.; Li, J.; Yu, D.-G. Acta Chim. Sinica 2019, 77, 783. (in Chinese)
[1]
(张振, 龚莉, 周晓渝, 颜思顺, 李静, 余达刚, 化学学报, 2019, 77, 783.)
[1]
(e) Gao, Y.; Wang, H.; Chi, Z.; Yang, L.; Zhou, C.; Li, G. CCS Chem. 2022, 4, 1565.
[2]
(a) Liu, Q.; Wu, L.; Jackstell, R.; Beller, M. Nat. Commun. 2015, 6, 5933.
[2]
(b) Burkart, M. D.; Hazari, N.; Tway, C. L.; Zeitler, E. L. ACS Catal. 2019, 9, 7937.
[2]
(c) Francis, A.; Priya, S. S.; Kumar, S. H.; Sudhakar, K.; Tahir, M. J. CO2 Util. 2021, 47, 101515.
[2]
(d) Li, H.-R.; He, L.-N. Organometallics 2020, 39, 1461.
[3]
(a) Banerjee, A.; Dick, G. R.; Yoshino, T.; Kanan, M. W. Nature 2016, 531, 215.
[3]
(b) Boogaerts, I. I. F.; Nolan, S. P. Chem. Commun. 2011, 47, 3021.
[3]
(c) Manjolinho, F.; Arndt, M.; Gooßen, K.; Gooßen, L. J. ACS Catal. 2012, 2, 2014.
[3]
(d) Qiao, C.; Cao, Y.; He, L.-N. Mini-Rev. Org. Chem. 2018, 15, 283.
[3]
(e) Tortajada, A.; Juliá-Hernández, F.; Börjesson, M.; Moragas, T.; Martin, R. Angew. Chem.,Int. Ed. 2018, 57, 15948.
[4]
(a) Kim, S. H.; Kim, K. H.; Hong, S. H. Angew. Chem., nt. Ed. 2014, 53, 771.
[4]
(b) Zhang, X.; Zhang, W.-Z.; Ren, X.; Zhang, L.-L.; Lu, X.-B. Org. Lett. 2011, 13, 2402.
[4]
(c) Guo, C.-X.; Yu, B.; Xie, J.-N.; He, L.-N. Green Chem. 2015, 17, 474.
[4]
(d) Arndt, M.; Risto, E.; Krause, T.; Gooßen, L. J. ChemCatChem 2012, 4, 484.
[5]
(a) Yuan, Y.; Chen, C.; Zeng, C.; Mousavi, B.; Chaemchuen, S.; Verpoort, F. ChemCatChem 2017, 9, 882.
[5]
(b) Wang, W.; Zhang, G.; Lang, R.; Xia, C.; Li, F. Green Chem. 2013, 15, 635.
[5]
(c) Li, S.; Sun, J.; Zhang, Z.; Xie, R.; Fang, X.; Zhou, M. Dalton Trans. 2016, 45, 10577.
[5]
(d) Bresciani, G.; Marchetti, F.; Pampaloni, G. New J. Chem. 2019, 43, 10821.
[6]
(a) Liu, X.-H.; Ma, J.-G.; Niu, Z.; Yang, G.-M.; Cheng, P. Angew. Chem.,Int. Ed. 2015, 54, 988.
[6]
(b) Wu, Z.; Sun, L.; Liu, Q.; Yang, X.; Ye, X.; Hu, Y; Huang, Y. A. Green Chem. 2017, 19, 2080.
[6]
(c) Wu, Z.; Liu, Q.; Yang, X.; Ye, X.; Duan, H.; Zhang, J.; Zhao, B.; Huang, Y. ACS Sustainable Chem. Eng. 2017, 5, 9634.
[6]
(d) Yu, D.; Tan, M. X.; Zhang, Y. Adv. Synth. Catal. 2012, 354, 969.
[7]
Saito, S.; Nakagawa, S.; Koizumi, T.; Hirayama, K.; Yamamoto, Y. J. Org. Chem. 1999, 64, 3975.
[8]
Chen, J.-H.; Deng, C.-H.; Fang, S.; Ma, J.-G.; Cheng, P. Green Chem. 2018, 20, 989.
[9]
Cheng, H.; Zhao, B.; Yao, Y.; Lu, C. Green Chem. 2015, 17, 1675.
[10]
Shi, J.-B.; Bu, Q.; Liu, B.-Y.; Dai, B.; Liu, N. J. Org. Chem. 2021, 86, 1850.
[11]
Fukue, Y.; Oi, S.; Inoue, Y. J. Chem. Soc., hem. Commun. 1994, 2091.
[12]
Inamoto, K.; Asano, N.; Kobayashi, K.; Yonemoto, M.; Kondo, Y. A. Org. Biomol. Chem. 2012, 10, 1514.
[13]
(a) Gooßen, L. J.; Rodríguez, N.; Manjolinho, F.; Lange, P. P. Adv. Synth. Catal. 2010, 352, 2913.
[13]
(b) Wendling, T.; Risto, E.; Krause, T.; Gooßen, L. J. Chem.-Eur. J. 2018, 24, 6019.
[14]
(a) Trivedi, M.; Singh, G.; Kumar, A.; Rath, N. P. Dalton Trans. 2015, 44, 20874.
[14]
(b) Trivedi, M.; Smreker, J. R.; Singh, G.; Kumar, A.; Rath, N. P. New J. Chem. 2017, 41, 14145.
[15]
Zhang, W.-Z.; Li, W.-J.; Zhang, X.; Zhou, H.; Lu, X.-B. Org. Lett. 2010, 12, 4748.
[16]
Yu, D.; Zhang, Y. Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 20184.
[17]
Yu, B.; Diao, Z.-F.; Guo, C.-X.; Zhong, C.-L.; He, L.-N.; Zhao, Y.-N.; Song, Q.-W.; Liu, A.-H.; Wang, J.-Q. Green Chem. 2013, 15, 2401.
[18]
Li, F.-W.; Suo, Q.-L.; Hong, H.-L.; Zhu, N.; Wang, Y.-Q.; Han, L.-M. Tetrahedron Lett. 2014, 55, 3878.
[19]
Yu, B.; Xie, J.-N.; Zhong, C.-L.; Li, W.; He, L.-N. ACS Catal. 2015, 5, 3940.
[20]
Chen, F.; Tao, S.; Deng, Q.-Q.; Wei, D.; Liu, N.; Dai, B. J. Org. Chem. 2020, 85, 15197.
[21]
(a) Zhang, L.; Cheng, J.; Ohishi, T.; Hou, Z. Angew. Chem., nt. Ed. 2010, 49, 8670.
[21]
(b) Inomata, H.; Ogata, K.; Fukuzawa, S.-I.; Hou, Z. Org. Lett. 2012, 14, 3986.
[21]
(c) Boogaerts, I. I. F.; Fortman, G. C.; Furst, M. R. L.; Cazin, C. S. J.; Nolan, S. P. Angew. Chem., nt. Ed. 2010, 49, 8674.
[21]
(d) Boogaerts, I. I. F.; Nolan, S. P. J. Am. Chem. Soc. 2010, 132, 8858.
[21]
(e) Vechorkin, O.; Hirt, N.; Hu, X. Org. Lett. 2010, 12, 3567.
[21]
(f) Ackermann, L. Angew. Chem., nt. Ed. 2011, 50, 3842.
[21]
(g) Fenner, S.; Ackermann, L. Green Chem. 2016, 18, 3804.
[22]
(a) Braunstein, P.; Naud, F. Angew. Chem., nt. Ed. 2001, 40, 680.
[22]
(b) Bailey, W. D.; Luconi, L.; Rossin, A.; Yakhvarov, D.; Flowers, S. E.; Kaminsky, W.; Kemp, R. A.; Giambastiani, G.; Goldberg, K. I. Organometallics 2015, 34, 3998.
[22]
(c) Fleckhaus, A.; Mousa, A. H.; Lawal, N. S.; Kazemifar, N. K.; Wendt, O. F. Organometallics 2015, 34, 1627.
[23]
Xie, J.-N.; Yu, B.; Zhou, Z.-H.; Fu, H.-C.; Wang, N.; He, L.-N. Tetrahedron Lett. 2015, 56, 7059.
[24]
Jover, J.; Maseras, F. J. Org. Chem. 2014, 79, 11981.
[25]
Yu, D.; Zhang, Y. Green Chem. 2011, 13, 1275.
[26]
Feng, Q.; Yang, K.; Song, Q. Chem. Commun. 2015, 51, 15394.
[27]
Yu, B.; Yang, P.; Gao, X.; Yang, Z. Z.; Zhao, Y. F.; Zhang, H. Y.; Liu, Z. M. C. New J. Chem. 2017, 41, 9250.
[28]
Wang, W.-H.; Feng, X.; Sui, K.; Fang, D.; Bao, M. J. CO2 Util. 2019, 32, 140.
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