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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 4: 1483 - 1491

DOI: https://doi.org/10.6023/cjoc202208031

ARTICLES

Ring Opening Amination of gem-Difluorocyclopropanes with Cyclobutanone Hydrazones

  • Zhipeng Liang ,
  • Hao Ye ,
  • Haibin Zhang ,
  • Guomin Jiang ,
  • Xinxing Wu
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  • a College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019
    b College of Pharmaceutical and Environmental Engineering, Nantong Vocational University, Nantong, Jiangsu 226019
    c Jiangsu Haofeng Bio-technology Co., Ltd., Nantong, Jiangsu 226019
* Corresponding author. ;

Received date: 2022-08-24

  Revised date: 2022-11-02

  Online published: 2022-12-12

Supported by

National Natural Science Foundation of China(22201145); Scientific Research Foundation of High-level Talents of Nantong University(03083031); Universities Natural Science Research Project of Jiangsu Province(21KJB150015); Large Instruments Open Foundation of Nantong University(KFJN2215)

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Abstract

N-Fluoroallyl hydrazones with four-ring structure were effectively synthesized using cyclobutanone hydrazones and gem-difluorocyclopropanes as raw materials through palladium catalyzed ring opening of difluorocyclopropanes and nucleophilic capture process of nitrogen nucleophile. This protocol shows broad substrate scope and good functional group tolerance, which can be applied for gram-scale preparation.

Key words： cyclobutanone hydrazone; gem-difluorocyclopropane; ring opening reaction; monofluoroalkene

Cite this article

Zhipeng Liang , Hao Ye , Haibin Zhang , Guomin Jiang , Xinxing Wu . Ring Opening Amination of gem-Difluorocyclopropanes with Cyclobutanone Hydrazones[J]. Chinese Journal of Organic Chemistry, 2023 , 43(4) : 1483 -1491 . DOI: 10.6023/cjoc202208031

References

[1]
(a) Hancock, E. N.; Wiest, J. M.; Brown, M. K. Nat. Prod. Rep. 2019, 36, 1383.
[1]
(b) Li, J.; Gao, K.; Bian, M.; Ding, H. Org. Chem. Front. 2020, 7, 136.
[1]
(c) Lukin, K.; Kishore, V.; Gordon, T. Org. Process Res. Dev. 2013, 17, 666.
[1]
(d) Beck, J. C.; Lacker, C. R.; Chapman, L. M.; Reisman, S. E. Chem. Sci. 2019, 10, 2315.
[1]
(e) Cui, Y.; Xia, D. Chin. J. Org. Chem. 2021, 41, 907. (in Chinese)
[1]
(崔英翠, 夏德斌, 有机化学, 2021, 41, 907.)
[2]
(a) Biletskyi, B.; Colonna, P.; Masson, K.; Parrain, J.-L.; Commeiras, L.; Chouraqui, G. Chem. Soc. Rev. 2021, 50, 7513.
[2]
(b) Murakami, M.; Ishida, N. Chem. Rev. 2021, 121, 264.
[3]
For selected examples: (a) Wang, Y.; Hu, M.; Ding, L.; Wang, Y.; Wang, X.-N.; Chang, J. Org. Lett. 2022, 24, 5056.
[3]
(b) Li, H.; Hsung, R. P.; DeKorver, K. A.; Wei, Y. Org. Lett. 2010, 12, 37806.
[3]
(c) K?lmel, D. K.; Ratnayake, A. S.; Flanagan, M. E.; Tsai, M.-H.; Duan, C.; Song, C. Org. Lett. 2020, 22, 2908.
[3]
(d) Luzung, M. R.; Mauleón, P.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 12402.
[3]
(e) Okamoto, K.; Shimbayashi, T.; Tamura, E.; Ohe, K. Org. Lett. 2015, 17, 5843.
[3]
(f) Oderinde, M. S.; Ramirez, A.; Murali Dhar, T. G.; L. A. M.; Jorge, C.; Aulakh, D.; Sandhu, B.; Pawluczyk, J.; Sarjeant, A. A.; Meanwell, N. A.; Mathur, A.; Kempson, J. J. Org. Chem. 2021, 86, 1730.
[3]
(g) Conner, M. L.; Kevin Brown, M. ; J. Org. Chem. 2016, 81, 8050.
[3]
(h) Zhu, H.-T.; Ke, S.; Zhou, N.-N.; Fan, M.-J.; Yang,, D.-S. Org. Lett. 2016, 18, 4554.
[3]
(i) Sakai, K.; Kochi, T.; Kakiuchi, F. Org. Lett. 2013, 15, 1024.
[4]
For selected examples: (a) Oishi, S.; Kamitani, H.; Kodama, E.; Matsuoka, M.; Fujii, N. Org. Biomol. Chem. 2009, 7, 2872.
[4]
(b) Fujita, T.; Fuchibe, K.; Ichikawa, J. Angew. Chem., Int. Ed. 2019, 58, 390.
[4]
(c) Osada, S.; Sano, S.; Ueyama, M.; Chuman, Y.; Kodama, H.; Sakaguchi, K. Bioorg. Med. Chem. 2010, 18, 605.
[4]
(d) Zhang, X.; Cao, S. Tetrahedron Lett. 2017, 58, 375.
[4]
(e) Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107.
[5]
For selected examples: (a) Dolbier, W. R.; Battiste, M. A. Chem. Rev. 2003, 103, 1071.
[5]
(b) Wenz, J.; Rettenmeier, C. A.; Wadepohl, H.; Gade, L. H. Chem. Commun. 2016, 52, 202.
[5]
(c) Song, X.; Xu, C.; Wang, M. Tetrahedron Lett. 2017, 58, 1806.
[5]
(d) Song, X.; Xu, C.; Du, D.; Zhao, Z.; Zhu, D.; Wang, M. Org. Lett. 2017, 19, 6542.
[5]
(e) Fu, Z.; Zhu, J.; Guo, S.; Lin, A. Chem. Commun. 2021, 57, 1262.
[5]
(f) Jiang, Z.-T.; Huang, J.; Zeng, Y.; Hu, F.; Xia, Y. Angew. Chem., Int. Ed. 2021, 60, 10626
[6]
For selected examples: (a) Ahmed, E.-A. M. A.; Suliman, A. M. Y.; Gong, T.-J.; Fu, Y. Org. Lett. 2019, 21, 5645.
[6]
(b) Ahmed, E.-A. M. A.; Suliman, A. M. Y.; Gong, T.-J.; Fu, Y. Org. Lett. 2020, 22, 1414.
[7]
Xu, J.; Ahmed, E.-A.; Xiao, B.; Lu, Q.-Q.; Wang, Y.-L.; Yu, C.-G.; Fu, Y. Angew. Chem., Int. Ed. 2015, 54, 8231.
[8]
Lv, L.; Li, C.-J. Angew. Chem., Int. Ed. 2021, 60, 13098.
[9]
Xiong, B.; Chen, X.; Liu, J.; Zhang, X.; Xia, Y.; Lian, Z. ACS Catal. 2021, 11, 11960.
[10]
(a) Ning, X.; Chen, Y.; Hu, F.; Xia, Y. Org. Lett. 2021, 23, 8348.
[10]
(b) Ye, H.; Ren, T.; Wu, X. Chin. J. Org. Chem. 2021, 41, 4338. (in Chinese)
[10]
(叶浩, 任婷婷, 吴新星, 有机化学, 2021, 41, 4338.)
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