Citation: Xukai Zhou, Jiaqiong Sun, Xingwei Li. Chemo-selective couplings of anilines and acroleins/enones under substrate control and condition control[J]. Chinese Journal of Catalysis, ;2018, 39(11): 1782-1791. doi: 10.1016/S1872-2067(18)63134-1 shu

Chemo-selective couplings of anilines and acroleins/enones under substrate control and condition control

a Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;
b University of Chinese Academy of Sciences, Beijing 100049, China

Received Date: 29 June 2018
Revised Date: 5 July 2018

Fund Project: This work was supported by the National Nature Science Foundation of China (21525208, 21472186) and the fund for new technology of methanol conversion of Dalian Institute of Chemical Physics (Chinese Academy of Sciences).

Rh(Ⅲ)-catalyzed C-H activation of N-protected anilines and chemo-divergent couplings with acroleins/enones have been realized for synthesis of three classes of heterocycles. The oxidative coupling of N-pyridylaniline afforded dihydroquinolones with the acrolein being a major hydrogen acceptor. When the directing group was replaced by pyrimidyl in the same system, redox-neutral coupling occurred to afford hemiaminal ethers. Oxidative annulation of N-pyridylanilines with enones using AgBF₄ oxidant afforded atropisomeric quinolinium salts.
- Rh(III)-catalysis,
- Chemo-selectivity,
- Annulation,
- Substrate control,
- Condition control
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
6. [6]
7. [7]
8. [8]
9. [9]
10. [10]
11. [11]
12. [12]
13. [13]
14. [14]
15. [15]
16. [16]
17. [17]
18. [18]
19. [19]
20. [20]
21. [21]
22. [22]
23. [23]
24. [24]
25. [25]
26. [26]
27. [27]
28. [28]
29. [29]
30. [30]
31. [31]
32. [32]
33. [33]
34. [34]
35. [35]
36. [36]
37. [37]
38. [38]
39. [39]
40. [40]
41. [41]
42. [42]
43. [43]
44. [44]
45. [45]
46. [46]
47. [47]
48. [48]
49. [49]
50. [50]
51. [51]
52. [52]
53. [53]
54. [54]
55. [55]
56. [56]
57. [57]
58. [58]
59. [59]
60. [60]
61. [61]
62. [62]
63. [63]
64. [64]
65. [65]
66. [66]
67. [67]
68. [68]
69. [69]
70. [70]
71. [71]
72. [72]
73. [73]
74. [74]
75. [75]
76. [76]
1. [1]
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