Citation: Zhiwei Xi, Liqiu Liu, Yingchun Wang. Recent Advances in Palladium Catalyzed Isocyanide Reactions[J]. Chemistry, ;2021, 84(5): 450-459. shu

Recent Advances in Palladium Catalyzed Isocyanide Reactions

College of Chemistry and Chemical Engineering, Hunan Engineering Laboratory for Analyse and Drugs Development of Ethnomedicine in Wuling Mountains, Jishou University, Jishou, 416000

Corresponding author: Yingchun Wang, wangyingchunjsu@163.com
Received Date: 27 September 2020
Accepted Date: 4 December 2020

Figures(22)

As an important class of active synthons in organic synthesis, isocyanide is used to synthesize natural products, drug molecules and nitrogen-containing molecules or heterocyclic compounds with potential biological activity. In recent years, palladium-catalyzed various reactions involving isocyanide, especially the insertion reaction of isocyanide, have been widely concerned, studied and applied, which is of great practical significance. In this review, according to different reaction types, the latest research progress in palladium-catalyzed isocyanide reactions is introduced.
- Isocyanide,
- Pd-catalysis,
- Insertion reaction,
- Coupling reaction,
- Tandem reaction
1. [1]
  Lieke W. Ann. Chem. Pharm., 1859, 112: 316~321.
2. [2]
3. [3]
4. [4]
5. [5]
  Boyarskiy V P, Bokach N A, Luzyanin K V, et al. Chem. Rev., 2015, 115(7): 2698~2779.
6. [6]
7. [7]
8. [8]
9. [9]
  Sadjadi S, Heravi M M, Nazari N. RSC Adv., 2016, 6(58): 53203~53272.
10. [10]
  Yurino T, Tani R, Ohkuma T. ACS Catal., 2019, 9(5): 4434~4440.
11. [11]
  Okumura S, Sun F Z, Ishida N, et al. J. Am. Chem. Soc., 2017, 139(36): 12414~12417.
12. [12]
  Du J, Huang Z M, Zhang Y N, et al. Chem. Eur. J., 2019, 25(43): 10149~10155.
13. [13]
  Ito Y, Ito I, Hirao T, et al. Synth. Commun., 1974, 4(2): 97~103.
14. [14]
15. [15]
16. [16]
  Collet J W, Roose T R, Ruijter E, et al. Angew. Chem. Int. Ed., 2019, 59(2): 540~558.
17. [17]
  Yang Q, Li C, Cheng M X, et al. ACS Catal., 2016, 6(7): 4715~4719.
18. [18]
  Li M, Fang S J, Zheng J, et al. Org. Lett., 2019, 21(20): 8439~8443.
19. [19]
  Chen B, Wu X F. Org. Lett., 2020, 22(2): 636~641.
20. [20]
  Chen Z B, Liu K, Zhang F L, et al. Org. Biomol. Chem., 2017, 15(38): 8078~8083.
21. [21]
  Clemenceau A, Wang Q, Zhu J P. Org. Lett., 2018, 20(1): 126~129.
22. [22]
  Wang X, Fu J P, Xie J X, et al. Org. Biomol. Chem., 2020, 18(26): 4936~4940.
23. [23]
  Otsuka S, Nogi K, Yorimitsu H. Angew. Chem. Int. Ed., 2018, 57(22): 6653~6657.
24. [24]
25. [25]
  Ito Y, Hirao T, Saegusa T. J. Org. Chem., 1975, 40(20): 2981~2982.
26. [26]
27. [27]
  Zhu F X, Li Y H, Wang Z C, et al. Chem. Eur. J., 2016, 22(23): 7743~7746.
28. [28]
  Lu F L, Chen Z Y, Li Z, et al. Org. Lett., 2017, 19(15): 3954~3957.
29. [29]
  Zhang Z, Li Z Y, Fu B, et al. Chem. Commun., 2015, 51(91): 16312~16315.
30. [30]
31. [31]
  Wang B, He D, Ren B G, et al. Chem. Commun., 2020, 56(6): 900~903.
32. [32]
  Hu W G, Li Z, Li J W, et al. Adv. Synth. Catal., 2017, 359(20): 3509~3514.
33. [33]
  Tao S W, Zhou J Y, Liu R Q, et al. J. Org. Chem., 2019, 84(12): 8121~8130.
34. [34]
  Dechert-Schmitt A, Garnsey M R, Wisniewska H M, et al. ACS Catal., 2019, 9(5): 4508~4515.
35. [35]
  Liu B, Gao H L, Yu Y, et al. J. Org. Chem., 2013, 78(20): 10319~10328.
36. [36]
  Chen Z, Duan H Q, Jiang X, et al. Synlett, 2014, 25(123): 1425~1430.
37. [37]
  Wang J, Tang S, Zhu Q. Org. Lett., 2016, 18(13): 3074~3077.
38. [38]
  Tang T, Fei X D, Ge Z Y, et al. J. Org. Chem., 2013, 78(7): 3170~3175.
39. [39]
  Curran D P, Du W. Org. Lett., 2002, 4(19): 3215~3218.
40. [40]
41. [41]
42. [42]
43. [43]
  Tong W, Li W H, He Y, et al. Org. Lett., 2018, 20(8): 2494~2498.
44. [44]
45. [45]
  Chen G S, Chen S J, Luo J, et al. Angew. Chem. Int. Ed., 2020, 59(2): 614~621.
46. [46]
  Song B R, Xu B. Chem. Soc. Rev., 2017, 46(4): 1103~1123.
47. [47]
  Luo S, Xiong Z, Lu Y Z, et al. Org. Lett., 2018, 20(7): 1837~1840.
48. [48]
  Tahara A, Nagino S, Sunada Y, et al. Organometallics, 2018, 37(15): 2531~2543.
49. [49]
50. [50]
  Liu Y L, Zhang K, Jiang W D, et al. Chem. Asian J., 2017, 12(5): 568~576.
51. [51]
  Huang H C, Qiu Z J, Han T, et al. ACS Macro Lett., 2017, 6(12): 1352~1356.
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