ARTICLES

Study on the Selective Difluorochloroethylation Reactions of Amides with Hypervalent Iodine Reagent

  • Tingxun Yan ,
  • Chao Chen ,
  • Lirong Wen
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  • a College of Chemistry and Molecular Engineering, Qingdao University of Science & Technology, Qingdao 266042
    b Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Ministry of Education,Department of Chemistry, Tsinghua University, Beijing 100084
    c State Key Laboratory of Elemental Organic Chemistry, Nankai University, Tianjin 300071
* Corresponding authors. E-mail: ;

Received date: 2021-04-04

  Revised date: 2021-05-17

  Online published: 2021-06-17

Supported by

National Key Research and Development Program of China(2016YFB0401400); National Natural Science Foundation of China(22071129); National Natural Science Foundation of China(21871158); National Natural Science Foundation of China(21672120); Fok Ying Tong Education Foundation of China(151014)

Abstract

Fluoroethylation products have a wide range of applications in the fields of biomedicine and materials, and the synthesis of fluorine-containing ethyl compounds is very important. At present, there are related reports on the synthesis of trifluoroethyl compounds, but there are few reports on how to synthesize difluoroethylated products. In this paper, through the reaction of chlorodifluoro iodine reagent and amide, N-chlorodifluoroethylation and O-chlorodifluoroethylation products were selectively generated. The selectivity of the reaction can be controlled by the choice of solvent, and the reaction is efficient, convenient and practical.

Cite this article

Tingxun Yan , Chao Chen , Lirong Wen . Study on the Selective Difluorochloroethylation Reactions of Amides with Hypervalent Iodine Reagent[J]. Chinese Journal of Organic Chemistry, 2021 , 41(9) : 3660 -3667 . DOI: 10.6023/cjoc202104007

References

[1]
(a) Kuduk, S. D.; Ng, C.; Du, F.; Wai, M.-C.; Chang, R.-S.; Harrell, C. M.; Murphy, K. L.; Ransom, R. W.; Reiss, D.; Ivarsson, M.; Mason, G.; Boyce, S.; Tang, C.; Prueksaritanont, T.; Freidinger, R. M.; Pettibone, D. J.; Bock, M. G. J. Med. Chem. 2004, 47, 6439.
[1]
(b) Zhang, J.; Jin, C.-F.; Zhang, Y.-J. Chin. J. Org. Chem. 2014, 34, 662. (in Chinese).
[1]
( 张霁, 金传飞, 张英俊, 有机化学, 2014, 34, 662.)
[1]
(c) Mwanwell, N, A. J. Med. Chem. 2011, 54, 2529.
[2]
Mcloughlin, V. C. R.; Thrower, J. Tetrahedron 1969, 25, 5921.
[3]
(a) Fujiwara, Y.; Dixon, J. A.; O'Hara, F.; Funder, E. D.; Dixon, D. D.; Rodriguez, R. A.; Baxter, R. D.; Herlé, B.; Sach, N.; Collins, M. R.; Ishihara, Y.; Baran, P. S. Nature 2012, 492, 95.
[3]
(b) Kreis, L. M. K.; Krautwald, S.; Pfeiffer, N.; Martin, R. E.; Carreira, E. M. Org. Lett. 2013, 15, 1634.
[4]
(a) Kreis, L. M. K.; Krautwald, S.; Pfeiffer, N.; Martin, R. E.; Carreira, E. M. Org. Lett. 2013, 15, 1634.
[4]
(b) Li, L.; Huang, M.; Liu, C.; Xiao, J.-C.; Chen, Q.-Y.; Guo, Y.; Zhao, Z.-G. Org. Lett. 2015, 17, 4714.
[4]
(c) Tang, X.-J.; Thomoson, S. C.; Dolbier, W. R. Org. Lett. 2014, 16, 4594.
[4]
(d) Roh, G. B.; Iqbal, N.; Cho, E. J. Chin. J. Chem. 2016, 34, 459.
[5]
(a) Zhao, Y.; Hu, J.-B. Angew. Chem., Int. Ed. 2012, 51, 1033.
[5]
(b) Liu, C.-B.; Meng, W.; Li, F.; Wang, S.; Nie, J.; Ma, J.-A. Angew. Chem., Int. Ed. 2012, 51, 6227.
[5]
(c) Zhang, H.; Chen, P.; Liu, G.-S. Angew. Chem., Int. Ed. 2014, 53, 10174.
[5]
(d) Song, W.; Lackner, S.; Ackermann, L. Angew. Chem., Int. Ed. 2014, 53, 2477.
[5]
(e) Ohtsuka, Y.; Yamakawa, T. J. Fluorine Chem. 2016, 185, 96.
[6]
(a) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
[6]
(b) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299.
[6]
(c) Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328.
[6]
(d) Han, Q.-Y.; Zhao, C.-L.; Zhang, C.-P. Chin. J. Org. Chem. 2019, 39, 84. (in Chinese).
[6]
( 韩秋燕, 赵成龙, 张成潘, 有机化学, 2019, 39, 84.)
[7]
(a) Umemoto, T.; Gotoh, Y. J. Fluorine Chem. 1985, 28, 235.
[7]
(b) Umemoto, T. Chem. Rev. 1996, 96, 1757.
[8]
(a) Zhdankin, V. V.; Kuehl, J.; Simonsen, A. J. J. Org. Chem. 1996, 61, 8272.
[8]
(b) DesMarteau, D. D.; Montanari, V. Chem. Commun. 1998, 2241.
[8]
(c) DesMarteau, D. D.; Montanari, V. Chem. Lett. 2000, 1052.
[8]
(d) DesMarteau, D. D.; Lu, C. Tetrahedron Lett. 2006, 47, 561.
[8]
(e) DesMarteau, D. D.; Lu, C. Chem. Commun. 2008, 208.
[8]
(f) Tolnai, G. L.; Székely, A.; Makó, Z.; Gáti, T.; Daru, J.; Bihari, T.; Stirling, A.; Novák, Z. Chem. Commun. 2015, 51, 4488.
[9]
Toth, B. L.; Kovacs, S.; Salyi, G.; Novak, Z. Angew. Chem., Int. Ed. 2016, 55, 1988.
[10]
(a) Lan, T.-L.; Qin, H.-J.; Chen, W.-T.; Liu, W.; Chen, C. Chin. Chem. Lett. 2020, 31, 357.
[10]
(b) Lan, T.-L.; Zhang, Y.; Liu, W.; Xi, C.-J.; Chen, C. Chin. J. Org. Chem. 2019, 39, 2166. (in Chinese).
[10]
( 兰天磊, 张越, 刘伟, 席婵娟, 陈超, 有机化学, 2019, 39, 2166.)
[10]
(c) Zhang, Y.; Lu, J.; Lan, T.-L.; Cheng, S.-L.; Liu, W.; Chen, C. Eur. J. Org. Chem. 2021, 3, 436.
[10]
(d) Liu, G.-X.-Z.; Wu, C.; Chen, B.-F.; He, R.; Chen, C. Chin. Chem. Lett. 2018, 29, 985.
[10]
(e) Chen, J.; Qu, H.-M.; Peng, J.; Chen, C. Chin. J. Org. Chem. 2015, 35, 937. (in Chinese).
[10]
( 陈静, 曲红梅, 彭静, 陈超, 有机化学, 2015, 35, 937.)
[11]
(a) Wang, Y.; Chen, C.; Peng, J.; Li, M. Angew. Chem., Int. Ed. 2013, 52, 5323.
[11]
(b) Chen, J.; Chen, C.; Wang, G.-H.; Qu, H.-M. Chem. Commun. 2015, 51, 1356.
[11]
(c) Sheng, J.-Y.; Wang, Y.; Su, X.; He, R.; Chen, C. Angew. Chem., Int. Ed. 2017, 56, 4824.
[11]
(d) Wang, G.-H.; Chen, C.; Peng, J. Chem. Commun. 2016, 52, 10277.
[11]
(e) Peng, J.; Chen, C.; Wang, Y.; Lou, Z.-B.; Li, M.; Xi, C.-J.; Chen, H. Angew. Chem., Int. Ed. 2013, 52, 7574.
[11]
(f) Dong, D.-Q.; Hao, S.-H.; Wang, Z.-L.; Chen, C. Org. Biomol. Chem. 2014, 12, 4278.
[11]
(g) Peng, J.; Chen, C.; Xi, C.-J. Chem. Sci. 2016, 7, 1383.
[11]
(h) Lin, J.-J.; Zhou, J.; Wu, P.-P; Chen, C. Eur. J. Org. Chem. 2019, 34, 5963.
[11]
(i) Su, X.; Sun, Y.-H.; Yao, J.-N.; Chen, H.; Chen, C. Chem. Commun. 2016, 52, 4537.
[11]
(j) Su, X.; Chen, C.; Wang, Y.; Chen, J.-J.; Lou, Z.-B.; Li, M. Chem. Commun. 2013, 49, 6752.
[11]
(k) Pang, X.-L.; Chen, C.; Su, X.; Li, M.; Wen, L.-R. Org. Lett. 2014, 16, 6228.
[11]
(l) Wu, C.; Zhao, C.-Y.; Zhou, J.; Hu, H.-S.; Li, J.; Wu, P.-P.; Chen, C. Commun. Chem. 2020, 3, 92.
[12]
(a) Cai, S.-J.; Chen, C.; Sun, Z.-L.; Xi, C.-J. Chem. Commun. 2013, 49, 4552.
[12]
(b) Cao, C. K.; Zhang, Y.; Lan, T.-L.; Liu, W.; Chen, C. Chem. Commun. 2019, 55, 9479.
[13]
Brisbois, R.G.; Wanke, R. A. e-EROS Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons ltd., New Jersey, 2013, pp. 1-6.
[14]
Umemoto, T.; Gotoh, Y. J. Fluorine Chem. 1986, 31, 231-236.
[15]
Chen, C.; Ge, C.-X.; Cao, C.-Y. CN 110128304, 2019.
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