Citation: Yaru Niu, Chengyao Kimmy Cao, Chenxin Ge, Hongmei Qu, Chao Chen. The Pd-catalyzed synthesis of difluoroethyl and difluorovinyl compounds with a chlorodifluoroethyl iodonium salt (CDFI)[J]. Chinese Chemical Letters, ;2022, 33(3): 1541-1544. doi: 10.1016/j.cclet.2021.09.004 shu

The Pd-catalyzed synthesis of difluoroethyl and difluorovinyl compounds with a chlorodifluoroethyl iodonium salt (CDFI)

Yaru Niu ^{a, b} ,
Chengyao Kimmy Cao ^b ,
Chenxin Ge ^b ,
Hongmei Qu ^{a, *,} ,
Chao Chen ^{b, c, *,}

a.
Key Laboratory of Systems Bioengineering, Ministry of Education, Department of Pharmaceutical Engineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350, China
b.
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education, MOE), Department of Chemistry, Tsinghua University, Beijing 100084, China
c.
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

ququhongmei@126.com

chenchao01@mails.tsinghua.edu.cn

Received Date: 23 July 2021
Revised Date: 29 August 2021
Accepted Date: 1 September 2021
Available Online: 9 September 2021

Figures(7)

Herein, we report a simple and efficient method for the direct installation of chlorodifluoroethyl group onto aromatic molecules of various aromatic amides with a new 2-chloro, 2, 2-difluoroethyl(mesityl)iodonium salt (CDFI). Moreover, the chlorodifluoroethyl compounds could be smoothly converted into difluorovinyl compounds in a one-pot or discrete procedure and regarded as a steady source of difluorovinyl compounds with "HCl-mask".
- Iodonium salts,
- C-H activation,
- Pd-catalyzed,
- Difluoroethylation,
- Difluorovinylation
1. [1]
  S. Caron, Org. Process. Res. Dev. 24 (2020) 470-480. doi: 10.1021/acs.oprd.0c00030
2. [2]
  C.N. Neumann, T. Ritter, Angew. Chem. Int. Ed. 54 (2015) 3216-3221. doi: 10.1002/anie.201410288
3. [3]
  N.A. Meanwell, J. Med. Chem. 61 (2018) 5822-5880. doi: 10.1021/acs.jmedchem.7b01788
4. [4]
  M.G. Campbell, T. Ritter, Org. Process. Res. Dev. 18 (2014) 474-480. doi: 10.1021/op400349g
5. [5]
  G. Chelucci, Chem. Rev. 112 (2012) 1344-1462. doi: 10.1021/cr200165q
6. [6]
  G. Magueur, D. Bonnet-Delpon, J.P. Bégué, J. Fluor. Chem. 127 (2006) 637-642. doi: 10.1016/j.jfluchem.2005.12.013
7. [7]
  X. Zhang, S. Cao, Tetrahedron Lett. 58 (2017) 375-392. doi: 10.1016/j.tetlet.2016.12.054
8. [8]
  M. Bobek, I. Kavai, E. De Clercq, J. Med. Chem. 30 (1987) 1494-1497. doi: 10.1021/jm00391a036
9. [9]
  N.A. Meanwell, J. Med. Chem. 54 (2011) 2529-2591. doi: 10.1021/jm1013693
10. [10]
  C. Leriche, X. He, C.W.T. Chang, H.W. Liu, J. Am. Chem. Soc. 125 (2003) 6348-6349. doi: 10.1021/ja021487+
11. [11]
  M.H. Lim, H.O. Kim, L.S. Jeong, et al., Org. Lett. 4 (2002) 529-531. doi: 10.1021/ol017112v
12. [12]
  H. Song, R. Cheng, Q.Q. Min, X.G. Zhang, Org. Lett. 22 (2020) 7747-7751. doi: 10.1021/acs.orglett.0c02997
13. [13]
  S.N. Jin, Z.J. Kuang, Q.L. Song, Org. Lett. 22 (2020) 615-619. doi: 10.1021/acs.orglett.9b04389
14. [14]
  Y. Wang, Y.H. Yang, C.Y. Wang, Chin. J. Chem. 37 (2019) 1229-1233. doi: 10.1002/cjoc.201900296
15. [15]
  M.L. Ke, Q.L. Song, J. Org. Chem. 81 (2016) 3654-3664. doi: 10.1021/acs.joc.6b00324
16. [16]
  S.M. Banik, J.W. Medley, E.N. Jacobsen, Science 353 (2016) 51-54. doi: 10.1126/science.aaf8078
17. [17]
  E. Miller, J. Am. Chem. Soc. 142 (2020) 8946-8952. doi: 10.1021/jacs.0c02331
18. [18]
  C. Luo, J.S. Bandar, J. Am. Chem. Soc. 141 (2019) 14120-14125. doi: 10.1021/jacs.9b07766
19. [19]
  R. Cheng, Y.Q. Sang, X. Gao, et al., Angew. Chem. Int. Ed. 60 (2021) 12386-12391. doi: 10.1002/anie.202015921
20. [20]
  R. Cheng, C. Xu, X.G. Zhang, Chin. J. Org. Chem. 40 (2020) 3307-3313. doi: 10.6023/cjoc202005082
21. [21]
  G.A. Wheaton, D.J. Burton, J. Org. Chem. 48 (1983) 917-927. doi: 10.1021/jo00155a001
22. [22]
  J. Zheng, J. Cai, J.C. Xiao, Chem. Commun. 49 (2013) 7513-7515. doi: 10.1039/c3cc44271c
23. [23]
  K. Aikawa, W. Toya, K. Mikami, Org. Lett. 17 (2015) 4996-4999. doi: 10.1021/acs.orglett.5b02439
24. [24]
  T. Fujita, Org. Lett. 22 (2020) 9253-9257. doi: 10.1021/acs.orglett.0c03476
25. [25]
  A. Yoshimura, V.V. Zhdankin, Chem. Rev. 116 (2016) 3328-3435. doi: 10.1021/acs.chemrev.5b00547
26. [26]
  I.F.D. Hyatt, Org. Biomol. Chem. 17 (2019) 7822-7848. doi: 10.1039/C9OB01267B
27. [27]
  S.E. Shetgaonkar, F.V. Singh, Front. Chem. 8 (2020) 705-729. doi: 10.3389/fchem.2020.00705
28. [28]
  S. Cai, C. Chen, C. Xi, et al., Chem. Commun. 49 (2013) 4552-4554. doi: 10.1039/c3cc41331d
29. [29]
  X. Shi, X. Li, D. Shi, et al., Front. Chem. 7 (2019) 613-622. doi: 10.3389/fchem.2019.00613
30. [30]
  Z. Gonda, Org. Lett. 16 (2014) 4268-4271. doi: 10.1021/ol501967c
31. [31]
  M.D. Levin, T.Q. Chen, M.E. Neubig, et al., Science 356 (2017) 1272-1276. doi: 10.1126/science.aan1411
32. [32]
  W. Song, S. Lackner, L. Ackermann, Angew. Chem. Int. Ed. 53 (2014) 2477-2480. doi: 10.1002/anie.201309584
33. [33]
  H. Zhang, P.H. Chen, G.S. Liu, Angew. Chem. Int. Ed. 53 (2014) 10174-10178. doi: 10.1002/anie.201403793
34. [34]
  P.S. Baran, Nature 492 (2012) 95-99. doi: 10.1038/nature11680
35. [35]
  B.L. Toth, S. Kovacs, Z. Novak, et al., Angew. Chem. Int. Ed. 55 (2016) 1988-1992. doi: 10.1002/anie.201510555
36. [36]
  Y. Wang, C. Chen, J. Peng, et al., Angew. Chem. Int. Ed. 52 (2013) 5323-5327. doi: 10.1002/anie.201300586
37. [37]
  D.Q. Dong, S.H. Hao, C. Chen, et al., Org. Biomol. Chem. 12 (2014) 4278-4289. doi: 10.1039/c4ob00318g
38. [38]
  J. Chen, C. Chen, H. Qu, et al., Chem. Commun. 51 (2015) 1356-1359. doi: 10.1039/C4CC08363F
39. [39]
  J. Peng, C. Chen, C. Xi, Chem. Sci. 7 (2016) 1383-1387. doi: 10.1039/C5SC03903G
40. [40]
  J. Sheng, Y. Wang, C. Chen, et al., Angew. Chem. Int. Ed. 56 (2017) 4824-4828. doi: 10.1002/anie.201700696
41. [41]
  J. Sheng, C. Wu, C. Chen, et al., Org. Lett. 20 (2018) 4458-4461. doi: 10.1021/acs.orglett.8b01748
42. [42]
  J. Lin, J. Zhou, C. Chen, et al., Eur. J. Org. Chem. 34 (2019) 5963-5969. doi: 10.1002/ejoc.201901017
43. [43]
  D.D. DesMarteau, V. Montanari, Chem. Commun. 20 (1998) 2241-2242. doi: 10.1039/A805879B
44. [44]
  T. Umemoto, Y. Gotoh, J. Fluor. Chem. 28 (1985) 235-239. doi: 10.1016/S0022-1139(00)81146-X
45. [45]
  J.D. Park, A.F. Benning, R.C. McHarness, et al., Ind. Eng. Chem. 39 (1947) 354-358. doi: 10.1021/ie50447a624
46. [46]
  J. Ichikawa, H. Miyazaki, Y. Wada, et al., J. Fluor. Chem. 125 (2004) 585-593. doi: 10.1016/j.jfluchem.2004.01.004
47. [47]
  M.J. Tozer, T.F. Herpin, Tetrahedron Lett. 52 (1996) 8619-8683. doi: 10.1016/0040-4020(96)00311-0
48. [48]
  S. Kovacs, B.L. Toth, Z Novak, et al., Adv. Synth. Catal. 359 (2017) 527-532. doi: 10.1002/adsc.201601136
49. [49]
  M. Maraswami, G. Chen, T.P. Loh, et al., Org. Lett. 19 (2017) 4223-4226. doi: 10.1021/acs.orglett.7b01859
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