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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 5: 1290 - 1296

DOI: https://doi.org/10.6023/cjoc201911020

One-Pot Synthesis of Unsymmetrical 1,4-Diaminobutynes by Cu(I)-Catalyzed Cross-Coupling of Propiolic Acid, Secondary Amine, Aldehydes and Formaldehyde

  • Liu Boyu ,
  • Xu Xianjun ,
  • Huang Liliang ,
  • Feng Huangdi
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  • College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620

Received date: 2019-11-12

  Revised date: 2020-01-21

  Online published: 2020-03-04

Supported by

Project supported by the Natural Science Foundation of Shanghai City (No. 15ZR1418800), the China Postdoctoral Science Foundation (No. 2016M601681), and the Shanghai University of Engineering Science (Nos. cs1704006, 201810856017).

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Abstract

A highly selective and efficient copper-catalyzed sequential approach for the one-pot two-step synthesis of unsymmetrical 1,4-diamino-2-butynes from propiolic acid, secondary alkylamine, aldehyde and formaldehyde solution has been developed. The process of this reaction was involved in the generation of key intermediate propargylamines which were obtained via decarboxylative A3-coupling reaction. After that, the intermediate propargylamines would react with in situ formed iminium ions to give the cross-coupling target products in moderate to excellent yields under microwave irradiation.

Key words： unsymmetrical diaminobutynes; decarboxylative coupling; A3-coupling; cross-coupling; copper-catalyzed

Cite this article

Liu Boyu , Xu Xianjun , Huang Liliang , Feng Huangdi . One-Pot Synthesis of Unsymmetrical 1,4-Diaminobutynes by Cu(I)-Catalyzed Cross-Coupling of Propiolic Acid, Secondary Amine, Aldehydes and Formaldehyde[J]. Chinese Journal of Organic Chemistry, 2020 , 40(5) : 1290 -1296 . DOI: 10.6023/cjoc201911020

References

[1] Volla, C. M.; Atodiresei, R. I.; Rueping, M. Chem. Rev. 2014, 114, 2390.
[2] Pellissier, H. Chem. Rev. 2013, 113, 442.
[3] Lu, L. Q.; Chen, J. R.; Xiao, W. J. Acc. Chem. Res. 2012, 45, 1278.
[4] Li, X. M.; Jia, X. S.; Yin, L. Chin. J. Org. Chem. 2017, 37, 2237(in Chinese). (李修明, 贾学顺, 殷亮, 有机化学, 2017, 37, 2237.)
[5] Trost, B. M. Acc. Chem. Res. 2002, 35, 695.
[6] Liu, S. Y.; Yao, W. F.; Liu, Y. Wei, Q. H., Chen, J. H.; Wu, X.; Xia, F.; Hu, W. H. Sci. Adv. 2017, 3, e1602467.
[7]
[7] Xu, J.; Fan, W. G.; Popowycz, F.; Queneau, Y.; Gu, Y. L. Chin. J. Org. Chem. 2019, 39, 2131(in Chinese). (徐静, 范维刚, 波波维奇·弗洛伦斯, 葛诺伊夫, 顾彦龙, 有机化学, 2019, 39, 2131.)
[8] Doemling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
[9] He, Y.; Li, Z. H.; Tian, G. L. Song, L. L.; Meervelt, L. V.; Van der Eycken, E. V. Chem. Commun. 2017, 53, 6413.
[10] Xu, R. Q.; Gu, Q.; You, S. L. Angew. Chem., Int. Ed. 2017, 56, 7252.
[11] Irudayanathan, F. M.; Lee, S. Org. Lett. 2017, 19, 2318.
[12] Feng, H. D.; Jia, H. H.; Sun, Z. H. Adv. Synth. Catal. 2015, 357, 2447.
[13] Priebbenow, D. L.; Becker, P.; Bolm, C. Org. Lett. 2013, 15, 6155.
[14]
[14] Zhang, J. Y.; Huang, X.; Shen, Q. Y.; Wang, J. Y.; Song, G. H. Chin. Chem. Lett. 2018, 29, 197.
[15] Feng, H. D.; Jia, H. H.; Sun, Z. H. J. Org. Chem. 2014, 79, 11812.
[16] Zhao, Y. W.; Feng, Q.; Song, Q. L. Chin. Chem. Lett. 2017, 27, 571.
[17] Wang, J. Y.; Shen, Q. Y.; Zhang, J. Y.; Song, G. H. Tetrahedron. Lett. 2015, 56, 903.
[18] Ermolat'ev, D. S.; Feng, H. D.; Song, G. H.; Van der Eycken, E. V. Eur. J. Org. Chem. 2014, 5346.
[19] Jayaraman, A.; Cho, E.; Francis, M. I; Jimin, K.; Lee, S. Adv. Synth. Catal. 2017, 360, 130.
[20] Shi, L. L.; Jia, W.; Li, X.; Jiao, L. Tetrahedron Lett. 2013, 54, 1951.
[21] Raja, G. C. E.; Irudayanathan, F. M.; Kim, H. S.; Lee, S. J. Org. Chem. 2016, 81, 5244.
[22] Park, K.; Bae, G.; Moon, J.; Choe, J.; Song, K. H.; Lee, S. J. Org. Chem. 2010, 75, 6244.
[23] Yu, M.; Pan, D. L.; Jia, W.; Chen, W.; Jiao, L. Tetrahedron Lett. 2010, 51, 1287.
[24] Kim, W.; Park, K.; Park, A.; Choe, J.; Lee, S. Org. Lett. 2013, 15, 1654.
[25] Moon, J.; Jeong, M.; Nam, H.; Ju, J. H.; Moon, J. H.; Jung, H. M.; Lee, S. Org. Lett. 2008, 10, 945.
[26] Feng, H. D.; Ermolat'ev, D. S.; Song, G. H.; Van der Eycken, E. V. J. Org. Chem. 2012, 77, 5149.
[27] Feng, H. D.; Zhao, P. F.; Huang, L. L.; Sun, Z. H. Asian J. Org. Chem. 2017, 6, 161.
[28] Feng, H. D.; Zhang, Y. Z.; Zhang, Z. D.; Chen, F. B.; Huang, L. L. Eur. J. Org. Chem. 2019, 1931
[29] Chen, C. L.; Wu, J. J.; Yan, G. B.; Huang, D. Y. Tetrahedron Lett. 2020, 61, 151415.
[30] Lee, Y.; Park, K.; Kim, H. S.; Kim, J. ARKIVOC 2016, V, 1.
[31] Zhao, W. J.; Huang, L.; Guan, Y.; Wulff, W. D. Angew. Chem., Int. Ed. 2014, 53, 3436.
[32] Zhao, P. F.; Feng, H. D.; Pan, H. R.; Sun, Z. H.; Tong, M. C. Org. Chem. Front. 2017, 4, 37.
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