Citation: Xiao-Bo Liu, Ren-Ming Liu, Xiao-Di Bao, Hua-Jian Xu, Qi Zhang, Yu-Feng Liang. Nickel-catalyzed reductive formylation of aryl halides via formyl radical[J]. Chinese Chemical Letters, ;2024, 35(12): 109783. doi: 10.1016/j.cclet.2024.109783 shu

Nickel-catalyzed reductive formylation of aryl halides via formyl radical

Xiao-Bo Liu ^{a, c} ,
Ren-Ming Liu ^c ,
Xiao-Di Bao ^c ,
Hua-Jian Xu ^{a, *,} ,
Qi Zhang ^{b, *,} ,
Yu-Feng Liang ^{c, *,}

a.
School of Food and Biological Engineering, School of Chemistry and Chemical Engineering, Anhui Province Key Laboratory of Advance Catalytic Materials and Reaction Engineering, Hefei University of Technology, Hefei 230009, China
b.
Institute of Industry & Equipment Technology, Hefei University of Technology, Hefei 230009, China
c.
School of Chemistry and Chemical Engineering, Shandong University, Ji'nan 250100, China

hjxu@hfut.edu.cn

zhangq@hfut.edu.cn

yfliang@sdu.edu.cn

Received Date: 29 November 2023
Revised Date: 2 March 2024
Accepted Date: 15 March 2024
Available Online: 20 March 2024

Figures(6)

Aromatic aldehydes are the most fundamentally important compounds used in organic synthesis. The development of new synthetic methods for introduction of a formyl group into an organic scaffold is highly desirable. In this report, a nickel-catalyzed reductive coupling between aryl halides and α–chloro N-methoxyphthalimide has been documented for the synthesis of a diverse array of aromatic aldehydes. Because of mild reductive coupling conditions, excellent functional group tolerance, especially for substrates containing free -OH and -NH₂, was observed. Due to the simple operation mode, a large library of aromatic aldehydes can be quickly constructed by this process. Moreover, the present protocol is amenable for late-stage functionalization of bioactive compound. A combined computational and experimental investigation suggested the reaction may undergo a reaction mechanism of active Ni(I) catalyst formation and the formation of key formyl radical intermediate under zinc reductive conditions.
- Nickel,
- Formylation,
- Radical,
- SET,
- Reductive coupling
References
1. [1]
  C.E.I. Knappke, S. Grupe, D. Gärtner, et al., Chem. Eur. J. 20 (2014) 6828–6842. doi: 10.1002/chem.201402302
2. [2]
  T. Moragas, A. Correa, R. Martin, Chem. Eur. J. 20 (2014) 8242–8258. doi: 10.1002/chem.201402509
3. [3]
  D.J. Weix, Acc. Chem. Res. 48 (2015) 1767–1775. doi: 10.1021/acs.accounts.5b00057
4. [4]
  J. Gu, X. Wang, W. Xue, H. Gong, Org. Chem. Front. 2 (2015) 1411–1421. doi: 10.1039/C5QO00224A
5. [5]
  E. Richmond, J. Moran, Synthesis 50 (2018) 499–513. doi: 10.1055/s-0036-1591853
6. [6]
  J. Liu, Y. Ye, J.L. Sessler, H. Gong, Acc. Chem. Res. 53 (2020) 1833–1845. doi: 10.1021/acs.accounts.0c00291
7. [7]
  K.E. Poremba, S.E. Dibrell, S.E. Reisman, ACS Catal. 10 (2020) 8237–8246. doi: 10.1021/acscatal.0c01842
8. [8]
  X. Pang, P.F. Su, X.Z. Shu, Acc. Chem. Res. 55 (2022) 2491–2509. doi: 10.1021/acs.accounts.2c00381
9. [9]
  Q. Pan, Y. Ping, W. Kong, Acc. Chem. Res. 56 (2023) 515–535. doi: 10.1021/acs.accounts.2c00771
10. [10]
  Y. Liu, P. Li, Y. Wang, Y. Qiu, Angew. Chem. Int. Ed. 62 (2023) e202306679. doi: 10.1002/anie.202306679
11. [11]
  J.L. Hofstra, A.H. Cherney, C.M. Ordner, S.E. Reisman, J. Am. Chem. Soc. 140 (2018) 139–142. doi: 10.1021/jacs.7b11707
12. [12]
  L.J. Oxtoby, Z.Q. Li, V.T. Tran, et al., Angew. Chem. Int. Ed. 59 (2020) 8885–8890. doi: 10.1002/anie.202001069
13. [13]
  F. Cong, X.Y. Lv, C.S. Day, R. Martin, J. Am. Chem. Soc. 142 (2020) 20594–20599. doi: 10.1021/jacs.0c11172
14. [14]
  X.W. Chen, J.P. Yue, K. Wang, et al., Angew. Chem. Int. Ed. 60 (2021) 14068–14075. doi: 10.1002/anie.202102769
15. [15]
  T.J. DeLano, S.E. Dibrell, C.R. Lacker, et al., Chem. Sci. 12 (2021) 7758–7762. doi: 10.1039/D1SC00822F
16. [16]
  S. Guven, G. Kundu, A. Weβels, et al., J. Am. Chem. Soc. 143 (2021) 8375–8380. doi: 10.1021/jacs.1c01797
17. [17]
  F. Wang, Y. Chen, W. Rao, L. Ackermann, S.Y. Wang, Nat. Commun. 13 (2022) 2588–2598. doi: 10.1038/s41467-022-30256-0
18. [18]
  Q. Wang, Q. Sun, Y. Jiang, et al., Nat. Synth. 1 (2022) 235–244. doi: 10.1038/s44160-022-00024-5
19. [19]
  Y.Z. Li, N. Rao, L. An, et al., Nat. Commun. 13 (2022) 5539–5547. doi: 10.1038/s41467-022-33159-2
20. [20]
  Z. Zhu, J. Xiao, M. Li, Z. Shi, Angew. Chem. Int. Ed. 61 (2022) e202201370. doi: 10.1002/anie.202201370
21. [21]
  Y. Dai, F. Wang, S. Zhu, L. Chu, Chin. Chem. Lett. 33 (2022) 4074–4078. doi: 10.1016/j.cclet.2021.12.050
22. [22]
  L. Xi, L. Du, Z. Shi, Chin. Chem. Lett. 33 (2022) 4287–4292. doi: 10.1016/j.cclet.2022.01.077
23. [23]
  Y. Wang, Z. Zhao, D. Pan, et al., Angew. Chem. Int. Ed. 61 (2022) e202210201. doi: 10.1002/anie.202210201
24. [24]
  X. Hu, I. Cheng-Sánchez, S. Cuesta-Galisteo, C. Nevado, J. Am. Chem. Soc. 145 (2023) 6270–6279. doi: 10.1021/jacs.2c12869
25. [25]
  Z.M. Su, J. Twilton, C.B. Hoyt, et al., ACS Cent. Sci. 9 (2023) 159–165. doi: 10.1021/acscentsci.2c01324
26. [26]
  X. Ying, Y. Li, L. Li, C. Li, Angew. Chem. Int. Ed. 62 (2023) e202304177. doi: 10.1002/anie.202304177
27. [27]
  W. Guan, L. Lu, Q. Jiang, et al., Angew. Chem. Int. Ed. 62 (2023) e202303592. doi: 10.1002/anie.202303592
28. [28]
  C.S. Day, A. Rentería-Gómez, S.J. Ton, et al., Nat. Catal. 6 (2023) 244–253. doi: 10.1038/s41929-023-00925-4
29. [29]
  J. Zhou, D. Wang, W. Xu, Z. Hu, T. Xu, J. Am. Chem. Soc. 145 (2023) 2081–2087. doi: 10.1021/jacs.2c13220
30. [30]
  L. Wan, Y. Tong, X. Lu, Y. Fu, Chin. Chem. Lett. 35 (2024) 109283. doi: 10.1016/j.cclet.2023.109283
31. [31]
  S.Z. Tasker, E.A. Standley, T.F. Jamison, Nature 509 (2014) 299–309. doi: 10.1038/nature13274
32. [32]
  J. Diccianni, Q. Lin, T. Diao, Acc. Chem. Res. 53 (2020) 906–919. doi: 10.1021/acs.accounts.0c00032
33. [33]
  N. Lalloo, C.E. Brigham, M.S. Sanford, Acc. Chem. Res. 55 (2022) 3430–3444. doi: 10.1021/acs.accounts.2c00496
34. [34]
  Q. Lin, E. Spielvogel, T. Diao, Chem 9 (2023) 1295–1308. doi: 10.1016/j.chempr.2023.02.010
35. [35]
  S. Biswas, D.J. Weix, J. Am. Chem. Soc. 135 (2013) 16192–16197. doi: 10.1021/ja407589e
36. [36]
  L.L. Anka-Lufford, K.M.M. Huihui, N.J. Gower, L.K.G. Ackerman, D.J. Weix, Chem. Eur. J. 22 (2016) 11564–11567. doi: 10.1002/chem.201602668
37. [37]
  S.Z. Sun, R. Martin, Angew. Chem. Int. Ed. 57 (2018) 3622–3625. doi: 10.1002/anie.201712428
38. [38]
  Y. Fang, T. Rogge, L. Ackermann, S.Y. Wang, S.J. Ji, Nat. Commun. 9 (2018) 2240–2250. doi: 10.1038/s41467-018-04646-2
39. [39]
  H. Yin, J. Sheng, K.F. Zhang, et al., Chem. Commun. 55 (2019) 7635–7638. doi: 10.1039/C9CC03737C
40. [40]
  S.J. He, J.W. Wang, Y. Li, et al., J. Am. Chem. Soc. 142 (2020) 214–221. doi: 10.1021/jacs.9b09415
41. [41]
  P. Fan, C. Zhang, L. Zhang, C. Wang, Org. Lett. 22 (2020) 3875–3878. doi: 10.1021/acs.orglett.0c01121
42. [42]
  D.J. Charboneau, E.L. Barth, N. Hazari, M.R. Uehling, S.L. Zultanski, ACS Catal 10 (2020) 12642–12656. doi: 10.1021/acscatal.0c03237
43. [43]
  H.Y. Tu, F. Wang, L. Huo, et al., J. Am. Chem. Soc. 142 (2020) 9604–9611. doi: 10.1021/jacs.0c03708
44. [44]
  D. Sun, G. Ma, X. Zhao, C. Lei, H. Gong, Chem. Sci. 12 (2021) 5253–5258. doi: 10.1039/D1SC00283J
45. [45]
  Z. Li, W. Sun, X. Wang, et al., J. Am. Chem. Soc. 143 (2021) 3536–3543. doi: 10.1021/jacs.0c13093
46. [46]
  P. Zheng, P. Zhou, D. Wang, et al., Nat. Commun. 12 (2021) 1646. doi: 10.1038/s41467-021-21947-1
47. [47]
  X. Li, X. Gao, C.Y. He, X. Zhang, Org. Lett. 23 (2021) 1400–1405. doi: 10.1021/acs.orglett.1c00058
48. [48]
  N.W.J. Ang, L. Ackermann, Chem. Eur. J. 27 (2021) 4883–4887. doi: 10.1002/chem.202005449
49. [49]
  R.F. Turro, M. Brandstätter, S.E. Reisman, Angew. Chem. Int. Ed. 61 (2022) e202207597. doi: 10.1002/anie.202207597
50. [50]
  W. Hu, Z. Lin, C. Wang, Org. Lett. 24 (2022) 5751–5755. doi: 10.1021/acs.orglett.2c02199
51. [51]
  Y. Gong, L. Su, Z. Zhu, Y. Ye, H. Gong, Angew. Chem. Int. Ed. 61 (2022) e202201662. doi: 10.1002/anie.202201662
52. [52]
  H. Wang, P. Zheng, X. Wu, Y. Li, T. Xu, J. Am. Chem. Soc. 144 (2022) 3989–3997. doi: 10.1021/jacs.1c12424
53. [53]
  D. Wang, L. Ackermann, Chem. Sci. 13 (2022) 7256–7263. doi: 10.1039/D2SC02277J
54. [54]
  W.T. Zhao, W. Shu, Sci. Adv. 9 (2023) eadg9898. doi: 10.1126/sciadv.adg9898
55. [55]
  J. Yi, S.O. Badir, L.M. Kammer, M. Ribagorda, G.A. Molander, Org. Lett. 21 (2019) 3346–3351. doi: 10.1021/acs.orglett.9b01097
56. [56]
  H. Yue, C. Zhu, L. Shen, et al., Chem. Sci. 10 (2019) 4430–4435. doi: 10.1039/C9SC00783K
57. [57]
  S. Ni, C.X. Li, Y. Mao, et al., Sci. Adv. 5 (2019) eaaw9516. doi: 10.1126/sciadv.aaw9516
58. [58]
  S.Z. Sun, C. Romano, R. Martin, J. Am. Chem. Soc. 141 (2019) 16197–16201. doi: 10.1021/jacs.9b07489
59. [59]
  S. Plunkett, C.H. Basch, S.O. Santana, M.P. Watson, J. Am. Chem. Soc. 141 (2019) 2257–2262. doi: 10.1021/jacs.9b00111
60. [60]
  J. Wang, M.E. Hoerrner, M.P. Watson, D.J. Weix, Angew. Chem. Int. Ed. 59 (2020) 13484–13489. doi: 10.1002/anie.202002271
61. [61]
  Y. Jin, J. Wu, Z. Lin, Y. Lan, C. Wang, Org. Lett. 22 (2020) 5347–5352. doi: 10.1021/acs.orglett.0c01592
62. [62]
  J.T.M. Correia, V.A. Fernandes, B.T. Matsuo, et al., Chem. Commun. 56 (2020) 503–514. doi: 10.1039/C9CC08348K
63. [63]
  J. Fu, W. Lundy, R. Chowdhury, et al., ACS Catal. 13 (2023) 9336–9345. doi: 10.1021/acscatal.3c01939
64. [64]
  J. Wang, L.E. Ehehalt, Z. Huang, et al., J. Am. Chem. Soc. 145 (2023) 9951–9958. doi: 10.1021/jacs.2c11552
65. [65]
  J.L. Douthwaite, R. Zhao, E. Shim, et al., J. Am. Chem. Soc. 145 (2023) 10930–10937. doi: 10.1021/jacs.2c11563
66. [66]
  A. Noble, S.J. McCarver, D.W.C. MacMillan, J. Am. Chem. Soc. 137 (2015) 624–627. doi: 10.1021/ja511913h
67. [67]
  J. Luo, J. Zhang, ACS Catal. 6 (2016) 873–877. doi: 10.1021/acscatal.5b02204
68. [68]
  H. Huang, X. Li, C. Yu, et al., Angew. Chem. Int. Ed. 56 (2017) 1500–1505. doi: 10.1002/anie.201610108
69. [69]
  Y. Hioki, M. Costantini, J. Griffin, et al., Science 380 (2023) 81–87. doi: 10.1126/science.adf4762
70. [70]
  M. Gao, D. Sun, H. Gong, Org. Lett. 21 (2019) 1645–1648. doi: 10.1021/acs.orglett.9b00174
71. [71]
  Y. Ye, H. Chen, J.L. Sessler, H. Gong, J. Am. Chem. Soc. 141 (2019) 820–824. doi: 10.1021/jacs.8b12801
72. [72]
  P. Guo, K. Wang, W.J. Jin, et al., J. Am. Chem. Soc. 143 (2021) 513–523. doi: 10.1021/jacs.0c12462
73. [73]
  X. Pang, X.Z. Shu, Chin. J. Chem. 41 (2023) 1637–1652. doi: 10.1002/cjoc.202200769
74. [74]
  K.M.M. Huihui, J.A. Caputo, Z. Melchor, et al., J. Am. Chem. Soc. 138 (2016) 5016–5019. doi: 10.1021/jacs.6b01533
75. [75]
  L. Huang, A.M. Olivares, D.J. Weix, Angew. Chem. Int. Ed. 56 (2017) 11901–11905. doi: 10.1002/anie.201706781
76. [76]
  J. Wang, B.P. Cary, P.D. Beyer, S.H. Gellman, D.J. Weix, Angew. Chem. Int. Ed. 58 (2019) 12081–12085. doi: 10.1002/anie.201906000
77. [77]
  Z. Li, K.F. Wang, X. Zhao, et al., Nat. Commun. 11 (2020) 5036. doi: 10.1038/s41467-020-18834-6
78. [78]
  L.M. Kammer, S.O. Badir, R.M. Hu, G.A. Molander, Chem. Sci. 12 (2021) 5450–5457. doi: 10.1039/D1SC00943E
79. [79]
  D.C. Salgueiro, B.K. Chi, I.A. Guzei, P. García-Reynaga, D.J. Weix, Angew. Chem. Int. Ed. 61 (2022) e202205673. doi: 10.1002/anie.202205673
80. [80]
  E.M. DeCicco, S. Berritt, T. Knauber, S.B. Coffey, J. Hou, J. Org. Chem. 88 (2023) 12329–12340. doi: 10.1021/acs.joc.3c01072
81. [81]
  Y. Gao, B. Zhang, J. He, P.S. Baran, J. Am. Chem. Soc. 145 (2023) 11518–11523. doi: 10.1021/jacs.3c03337
82. [82]
  A. Schoenberg, I. Bartolet, R.F. Heck, J. Org. Chem. 39 (1974) 3318–3326. doi: 10.1021/jo00937a003
83. [83]
  W. Wu, W. Su, J. Am. Chem. Soc. 133 (2011) 11924–11927. doi: 10.1021/ja2048495
84. [84]
  T. Ueda, H. Konishi, K. Manabe, Angew. Chem. Int. Ed. 52 (2013) 8611–8615. doi: 10.1002/anie.201303926
85. [85]
  B. Zhao, R. Shang, W.M. Cheng, Y. Fu, Org. Chem. Front. 5 (2018) 1782–1786. doi: 10.1039/C8QO00253C
86. [86]
  S. Klaus, H. Neumann, A. Zapf, et al., Angew. Chem. Int. Ed. 45 (2006) 154–158. doi: 10.1002/anie.200502697
87. [87]
  A. Brennfãhrer, H. Neumann, M. Beller, Synlett 16 (2007) 2537–2540.
88. [88]
  A.G. Sergeev, A. Spannenberg, M. Beller, J. Am. Chem. Soc. 130 (2008) 15549–15563. doi: 10.1021/ja804997z
89. [89]
  S. Korsager, R.H. Taaning, T. Skrydstrup, J. Am. Chem. Soc. 135 (2013) 2891–2894. doi: 10.1021/ja3114032
90. [90]
  K. Natte, A. Dumrath, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 53 (2014) 10090–10094. doi: 10.1002/anie.201404833
91. [91]
  Z. Liu, Z. Yang, B. Yu, et al., Org. Lett. 20 (2018) 5130–5134. doi: 10.1021/acs.orglett.8b02027
92. [92]
  D. Liu, K. Yang, D. Fang, et al., Angew. Chem. Int. Ed. 62 (2023) e202213686. doi: 10.1002/anie.202213686
93. [93]
  C.T. Wang, P.Y. Liang, M. Li, et al., Angew. Chem. Int. Ed. 62 (2023) e202304447. doi: 10.1002/anie.202304447
94. [94]
  J. Sheng, X. Cheng, CCS Chem. 6 (2024) 230–240. doi: 10.31635/ccschem.023.202302835
95. [95]
  J. Choi, P. Martín-Gago, G.C. Fu, J. Am. Chem. Soc. 136 (2014) 12161–12165. doi: 10.1021/ja506885s
96. [96]
  L. Lombardi, A. Cerveri, R. Giovanelli, et al., Angew. Chem. Int. Ed. 61 (2022) e202211732. doi: 10.1002/anie.202211732
97. [97]
  G. Bertoli, Á.M. Martínez, J.F. Goebel, et al., Angew. Chem. Int. Ed. 62 (2023) e202215920. doi: 10.1002/anie.202215920
98. [98]
  R.F. Turro, J.L.H. Wahlman, Z.J. Tong, et al., J. Am. Chem. Soc. 145 (2023) 14705–14715. doi: 10.1021/jacs.3c02649
1. [1]
  C.E.I. Knappke, S. Grupe, D. Gärtner, et al., Chem. Eur. J. 20 (2014) 6828–6842. doi: 10.1002/chem.201402302
2. [2]
  T. Moragas, A. Correa, R. Martin, Chem. Eur. J. 20 (2014) 8242–8258. doi: 10.1002/chem.201402509
3. [3]
  D.J. Weix, Acc. Chem. Res. 48 (2015) 1767–1775. doi: 10.1021/acs.accounts.5b00057
4. [4]
  J. Gu, X. Wang, W. Xue, H. Gong, Org. Chem. Front. 2 (2015) 1411–1421. doi: 10.1039/C5QO00224A
5. [5]
  E. Richmond, J. Moran, Synthesis 50 (2018) 499–513. doi: 10.1055/s-0036-1591853
6. [6]
  J. Liu, Y. Ye, J.L. Sessler, H. Gong, Acc. Chem. Res. 53 (2020) 1833–1845. doi: 10.1021/acs.accounts.0c00291
7. [7]
  K.E. Poremba, S.E. Dibrell, S.E. Reisman, ACS Catal. 10 (2020) 8237–8246. doi: 10.1021/acscatal.0c01842
8. [8]
  X. Pang, P.F. Su, X.Z. Shu, Acc. Chem. Res. 55 (2022) 2491–2509. doi: 10.1021/acs.accounts.2c00381
9. [9]
  Q. Pan, Y. Ping, W. Kong, Acc. Chem. Res. 56 (2023) 515–535. doi: 10.1021/acs.accounts.2c00771
10. [10]
  Y. Liu, P. Li, Y. Wang, Y. Qiu, Angew. Chem. Int. Ed. 62 (2023) e202306679. doi: 10.1002/anie.202306679
11. [11]
  J.L. Hofstra, A.H. Cherney, C.M. Ordner, S.E. Reisman, J. Am. Chem. Soc. 140 (2018) 139–142. doi: 10.1021/jacs.7b11707
12. [12]
  L.J. Oxtoby, Z.Q. Li, V.T. Tran, et al., Angew. Chem. Int. Ed. 59 (2020) 8885–8890. doi: 10.1002/anie.202001069
13. [13]
  F. Cong, X.Y. Lv, C.S. Day, R. Martin, J. Am. Chem. Soc. 142 (2020) 20594–20599. doi: 10.1021/jacs.0c11172
14. [14]
  X.W. Chen, J.P. Yue, K. Wang, et al., Angew. Chem. Int. Ed. 60 (2021) 14068–14075. doi: 10.1002/anie.202102769
15. [15]
  T.J. DeLano, S.E. Dibrell, C.R. Lacker, et al., Chem. Sci. 12 (2021) 7758–7762. doi: 10.1039/D1SC00822F
16. [16]
  S. Guven, G. Kundu, A. Weβels, et al., J. Am. Chem. Soc. 143 (2021) 8375–8380. doi: 10.1021/jacs.1c01797
17. [17]
  F. Wang, Y. Chen, W. Rao, L. Ackermann, S.Y. Wang, Nat. Commun. 13 (2022) 2588–2598. doi: 10.1038/s41467-022-30256-0
18. [18]
  Q. Wang, Q. Sun, Y. Jiang, et al., Nat. Synth. 1 (2022) 235–244. doi: 10.1038/s44160-022-00024-5
19. [19]
  Y.Z. Li, N. Rao, L. An, et al., Nat. Commun. 13 (2022) 5539–5547. doi: 10.1038/s41467-022-33159-2
20. [20]
  Z. Zhu, J. Xiao, M. Li, Z. Shi, Angew. Chem. Int. Ed. 61 (2022) e202201370. doi: 10.1002/anie.202201370
21. [21]
  Y. Dai, F. Wang, S. Zhu, L. Chu, Chin. Chem. Lett. 33 (2022) 4074–4078. doi: 10.1016/j.cclet.2021.12.050
22. [22]
  L. Xi, L. Du, Z. Shi, Chin. Chem. Lett. 33 (2022) 4287–4292. doi: 10.1016/j.cclet.2022.01.077
23. [23]
  Y. Wang, Z. Zhao, D. Pan, et al., Angew. Chem. Int. Ed. 61 (2022) e202210201. doi: 10.1002/anie.202210201
24. [24]
  X. Hu, I. Cheng-Sánchez, S. Cuesta-Galisteo, C. Nevado, J. Am. Chem. Soc. 145 (2023) 6270–6279. doi: 10.1021/jacs.2c12869
25. [25]
  Z.M. Su, J. Twilton, C.B. Hoyt, et al., ACS Cent. Sci. 9 (2023) 159–165. doi: 10.1021/acscentsci.2c01324
26. [26]
  X. Ying, Y. Li, L. Li, C. Li, Angew. Chem. Int. Ed. 62 (2023) e202304177. doi: 10.1002/anie.202304177
27. [27]
  W. Guan, L. Lu, Q. Jiang, et al., Angew. Chem. Int. Ed. 62 (2023) e202303592. doi: 10.1002/anie.202303592
28. [28]
  C.S. Day, A. Rentería-Gómez, S.J. Ton, et al., Nat. Catal. 6 (2023) 244–253. doi: 10.1038/s41929-023-00925-4
29. [29]
  J. Zhou, D. Wang, W. Xu, Z. Hu, T. Xu, J. Am. Chem. Soc. 145 (2023) 2081–2087. doi: 10.1021/jacs.2c13220
30. [30]
  L. Wan, Y. Tong, X. Lu, Y. Fu, Chin. Chem. Lett. 35 (2024) 109283. doi: 10.1016/j.cclet.2023.109283
31. [31]
  S.Z. Tasker, E.A. Standley, T.F. Jamison, Nature 509 (2014) 299–309. doi: 10.1038/nature13274
32. [32]
  J. Diccianni, Q. Lin, T. Diao, Acc. Chem. Res. 53 (2020) 906–919. doi: 10.1021/acs.accounts.0c00032
33. [33]
  N. Lalloo, C.E. Brigham, M.S. Sanford, Acc. Chem. Res. 55 (2022) 3430–3444. doi: 10.1021/acs.accounts.2c00496
34. [34]
  Q. Lin, E. Spielvogel, T. Diao, Chem 9 (2023) 1295–1308. doi: 10.1016/j.chempr.2023.02.010
35. [35]
  S. Biswas, D.J. Weix, J. Am. Chem. Soc. 135 (2013) 16192–16197. doi: 10.1021/ja407589e
36. [36]
  L.L. Anka-Lufford, K.M.M. Huihui, N.J. Gower, L.K.G. Ackerman, D.J. Weix, Chem. Eur. J. 22 (2016) 11564–11567. doi: 10.1002/chem.201602668
37. [37]
  S.Z. Sun, R. Martin, Angew. Chem. Int. Ed. 57 (2018) 3622–3625. doi: 10.1002/anie.201712428
38. [38]
  Y. Fang, T. Rogge, L. Ackermann, S.Y. Wang, S.J. Ji, Nat. Commun. 9 (2018) 2240–2250. doi: 10.1038/s41467-018-04646-2
39. [39]
  H. Yin, J. Sheng, K.F. Zhang, et al., Chem. Commun. 55 (2019) 7635–7638. doi: 10.1039/C9CC03737C
40. [40]
  S.J. He, J.W. Wang, Y. Li, et al., J. Am. Chem. Soc. 142 (2020) 214–221. doi: 10.1021/jacs.9b09415
41. [41]
  P. Fan, C. Zhang, L. Zhang, C. Wang, Org. Lett. 22 (2020) 3875–3878. doi: 10.1021/acs.orglett.0c01121
42. [42]
  D.J. Charboneau, E.L. Barth, N. Hazari, M.R. Uehling, S.L. Zultanski, ACS Catal 10 (2020) 12642–12656. doi: 10.1021/acscatal.0c03237
43. [43]
  H.Y. Tu, F. Wang, L. Huo, et al., J. Am. Chem. Soc. 142 (2020) 9604–9611. doi: 10.1021/jacs.0c03708
44. [44]
  D. Sun, G. Ma, X. Zhao, C. Lei, H. Gong, Chem. Sci. 12 (2021) 5253–5258. doi: 10.1039/D1SC00283J
45. [45]
  Z. Li, W. Sun, X. Wang, et al., J. Am. Chem. Soc. 143 (2021) 3536–3543. doi: 10.1021/jacs.0c13093
46. [46]
  P. Zheng, P. Zhou, D. Wang, et al., Nat. Commun. 12 (2021) 1646. doi: 10.1038/s41467-021-21947-1
47. [47]
  X. Li, X. Gao, C.Y. He, X. Zhang, Org. Lett. 23 (2021) 1400–1405. doi: 10.1021/acs.orglett.1c00058
48. [48]
  N.W.J. Ang, L. Ackermann, Chem. Eur. J. 27 (2021) 4883–4887. doi: 10.1002/chem.202005449
49. [49]
  R.F. Turro, M. Brandstätter, S.E. Reisman, Angew. Chem. Int. Ed. 61 (2022) e202207597. doi: 10.1002/anie.202207597
50. [50]
  W. Hu, Z. Lin, C. Wang, Org. Lett. 24 (2022) 5751–5755. doi: 10.1021/acs.orglett.2c02199
51. [51]
  Y. Gong, L. Su, Z. Zhu, Y. Ye, H. Gong, Angew. Chem. Int. Ed. 61 (2022) e202201662. doi: 10.1002/anie.202201662
52. [52]
  H. Wang, P. Zheng, X. Wu, Y. Li, T. Xu, J. Am. Chem. Soc. 144 (2022) 3989–3997. doi: 10.1021/jacs.1c12424
53. [53]
  D. Wang, L. Ackermann, Chem. Sci. 13 (2022) 7256–7263. doi: 10.1039/D2SC02277J
54. [54]
  W.T. Zhao, W. Shu, Sci. Adv. 9 (2023) eadg9898. doi: 10.1126/sciadv.adg9898
55. [55]
  J. Yi, S.O. Badir, L.M. Kammer, M. Ribagorda, G.A. Molander, Org. Lett. 21 (2019) 3346–3351. doi: 10.1021/acs.orglett.9b01097
56. [56]
  H. Yue, C. Zhu, L. Shen, et al., Chem. Sci. 10 (2019) 4430–4435. doi: 10.1039/C9SC00783K
57. [57]
  S. Ni, C.X. Li, Y. Mao, et al., Sci. Adv. 5 (2019) eaaw9516. doi: 10.1126/sciadv.aaw9516
58. [58]
  S.Z. Sun, C. Romano, R. Martin, J. Am. Chem. Soc. 141 (2019) 16197–16201. doi: 10.1021/jacs.9b07489
59. [59]
  S. Plunkett, C.H. Basch, S.O. Santana, M.P. Watson, J. Am. Chem. Soc. 141 (2019) 2257–2262. doi: 10.1021/jacs.9b00111
60. [60]
  J. Wang, M.E. Hoerrner, M.P. Watson, D.J. Weix, Angew. Chem. Int. Ed. 59 (2020) 13484–13489. doi: 10.1002/anie.202002271
61. [61]
  Y. Jin, J. Wu, Z. Lin, Y. Lan, C. Wang, Org. Lett. 22 (2020) 5347–5352. doi: 10.1021/acs.orglett.0c01592
62. [62]
  J.T.M. Correia, V.A. Fernandes, B.T. Matsuo, et al., Chem. Commun. 56 (2020) 503–514. doi: 10.1039/C9CC08348K
63. [63]
  J. Fu, W. Lundy, R. Chowdhury, et al., ACS Catal. 13 (2023) 9336–9345. doi: 10.1021/acscatal.3c01939
64. [64]
  J. Wang, L.E. Ehehalt, Z. Huang, et al., J. Am. Chem. Soc. 145 (2023) 9951–9958. doi: 10.1021/jacs.2c11552
65. [65]
  J.L. Douthwaite, R. Zhao, E. Shim, et al., J. Am. Chem. Soc. 145 (2023) 10930–10937. doi: 10.1021/jacs.2c11563
66. [66]
  A. Noble, S.J. McCarver, D.W.C. MacMillan, J. Am. Chem. Soc. 137 (2015) 624–627. doi: 10.1021/ja511913h
67. [67]
  J. Luo, J. Zhang, ACS Catal. 6 (2016) 873–877. doi: 10.1021/acscatal.5b02204
68. [68]
  H. Huang, X. Li, C. Yu, et al., Angew. Chem. Int. Ed. 56 (2017) 1500–1505. doi: 10.1002/anie.201610108
69. [69]
  Y. Hioki, M. Costantini, J. Griffin, et al., Science 380 (2023) 81–87. doi: 10.1126/science.adf4762
70. [70]
  M. Gao, D. Sun, H. Gong, Org. Lett. 21 (2019) 1645–1648. doi: 10.1021/acs.orglett.9b00174
71. [71]
  Y. Ye, H. Chen, J.L. Sessler, H. Gong, J. Am. Chem. Soc. 141 (2019) 820–824. doi: 10.1021/jacs.8b12801
72. [72]
  P. Guo, K. Wang, W.J. Jin, et al., J. Am. Chem. Soc. 143 (2021) 513–523. doi: 10.1021/jacs.0c12462
73. [73]
  X. Pang, X.Z. Shu, Chin. J. Chem. 41 (2023) 1637–1652. doi: 10.1002/cjoc.202200769
74. [74]
  K.M.M. Huihui, J.A. Caputo, Z. Melchor, et al., J. Am. Chem. Soc. 138 (2016) 5016–5019. doi: 10.1021/jacs.6b01533
75. [75]
  L. Huang, A.M. Olivares, D.J. Weix, Angew. Chem. Int. Ed. 56 (2017) 11901–11905. doi: 10.1002/anie.201706781
76. [76]
  J. Wang, B.P. Cary, P.D. Beyer, S.H. Gellman, D.J. Weix, Angew. Chem. Int. Ed. 58 (2019) 12081–12085. doi: 10.1002/anie.201906000
77. [77]
  Z. Li, K.F. Wang, X. Zhao, et al., Nat. Commun. 11 (2020) 5036. doi: 10.1038/s41467-020-18834-6
78. [78]
  L.M. Kammer, S.O. Badir, R.M. Hu, G.A. Molander, Chem. Sci. 12 (2021) 5450–5457. doi: 10.1039/D1SC00943E
79. [79]
  D.C. Salgueiro, B.K. Chi, I.A. Guzei, P. García-Reynaga, D.J. Weix, Angew. Chem. Int. Ed. 61 (2022) e202205673. doi: 10.1002/anie.202205673
80. [80]
  E.M. DeCicco, S. Berritt, T. Knauber, S.B. Coffey, J. Hou, J. Org. Chem. 88 (2023) 12329–12340. doi: 10.1021/acs.joc.3c01072
81. [81]
  Y. Gao, B. Zhang, J. He, P.S. Baran, J. Am. Chem. Soc. 145 (2023) 11518–11523. doi: 10.1021/jacs.3c03337
82. [82]
  A. Schoenberg, I. Bartolet, R.F. Heck, J. Org. Chem. 39 (1974) 3318–3326. doi: 10.1021/jo00937a003
83. [83]
  W. Wu, W. Su, J. Am. Chem. Soc. 133 (2011) 11924–11927. doi: 10.1021/ja2048495
84. [84]
  T. Ueda, H. Konishi, K. Manabe, Angew. Chem. Int. Ed. 52 (2013) 8611–8615. doi: 10.1002/anie.201303926
85. [85]
  B. Zhao, R. Shang, W.M. Cheng, Y. Fu, Org. Chem. Front. 5 (2018) 1782–1786. doi: 10.1039/C8QO00253C
86. [86]
  S. Klaus, H. Neumann, A. Zapf, et al., Angew. Chem. Int. Ed. 45 (2006) 154–158. doi: 10.1002/anie.200502697
87. [87]
  A. Brennfãhrer, H. Neumann, M. Beller, Synlett 16 (2007) 2537–2540.
88. [88]
  A.G. Sergeev, A. Spannenberg, M. Beller, J. Am. Chem. Soc. 130 (2008) 15549–15563. doi: 10.1021/ja804997z
89. [89]
  S. Korsager, R.H. Taaning, T. Skrydstrup, J. Am. Chem. Soc. 135 (2013) 2891–2894. doi: 10.1021/ja3114032
90. [90]
  K. Natte, A. Dumrath, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 53 (2014) 10090–10094. doi: 10.1002/anie.201404833
91. [91]
  Z. Liu, Z. Yang, B. Yu, et al., Org. Lett. 20 (2018) 5130–5134. doi: 10.1021/acs.orglett.8b02027
92. [92]
  D. Liu, K. Yang, D. Fang, et al., Angew. Chem. Int. Ed. 62 (2023) e202213686. doi: 10.1002/anie.202213686
93. [93]
  C.T. Wang, P.Y. Liang, M. Li, et al., Angew. Chem. Int. Ed. 62 (2023) e202304447. doi: 10.1002/anie.202304447
94. [94]
  J. Sheng, X. Cheng, CCS Chem. 6 (2024) 230–240. doi: 10.31635/ccschem.023.202302835
95. [95]
  J. Choi, P. Martín-Gago, G.C. Fu, J. Am. Chem. Soc. 136 (2014) 12161–12165. doi: 10.1021/ja506885s
96. [96]
  L. Lombardi, A. Cerveri, R. Giovanelli, et al., Angew. Chem. Int. Ed. 61 (2022) e202211732. doi: 10.1002/anie.202211732
97. [97]
  G. Bertoli, Á.M. Martínez, J.F. Goebel, et al., Angew. Chem. Int. Ed. 62 (2023) e202215920. doi: 10.1002/anie.202215920
98. [98]
  R.F. Turro, J.L.H. Wahlman, Z.J. Tong, et al., J. Am. Chem. Soc. 145 (2023) 14705–14715. doi: 10.1021/jacs.3c02649
1. [1]
  Jiangping Chen , Hongju Ren , Kai Wu , Huihuang Fang , Chongqi Chen , Li Lin , Yu Luo , Lilong Jiang . Boosting hydrogen production of ammonia decomposition via the construction of metal-oxide interfaces. Chinese Journal of Structural Chemistry, 2024, 43(2): 100236-100236. doi: 10.1016/j.cjsc.2024.100236
2. [2]
  Zhengzhong Zhu , Shaojun Hu , Zhi Liu , Lipeng Zhou , Chongbin Tian , Qingfu Sun . A cationic radical lanthanide organic tetrahedron with remarkable coordination enhanced radical stability. Chinese Chemical Letters, 2025, 36(2): 109641-. doi: 10.1016/j.cclet.2024.109641
3. [3]
  Zhenkang Ai , Hui Chen , Xuebin Liao . Nickel-catalyzed decarboxylative difluoromethylation and alkylation of alkenes. Chinese Chemical Letters, 2025, 36(3): 109954-. doi: 10.1016/j.cclet.2024.109954
4. [4]
  Shaobin He , Xiaoyun Guo , Qionghua Zheng , Huanran Shen , Yuan Xu , Fenglin Lin , Jincheng Chen , Haohua Deng , Yiming Zeng , Wei Chen . Engineering nickel-supported osmium bimetallic nanozymes with specifically improved peroxidase-like activity for immunoassay. Chinese Chemical Letters, 2025, 36(4): 110096-. doi: 10.1016/j.cclet.2024.110096
5. [5]
  Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
6. [6]
  Le Zhang , Hui-Yu Xie , Xin Li , Li-Ying Sun , Ying-Feng Han . SOMO-HOMO level conversion in triarylmethyl-cored N-heterocyclic carbene-Au(I) complexes triggered by selecting coordination halogens. Chinese Chemical Letters, 2024, 35(11): 109465-. doi: 10.1016/j.cclet.2023.109465
7. [7]
  Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
8. [8]
  Yuhan Liu , Jingyang Zhang , Gongming Yang , Jian Wang . Highly enantioselective carbene-catalyzed δ-lactonization via radical relay cross-coupling. Chinese Chemical Letters, 2025, 36(1): 109790-. doi: 10.1016/j.cclet.2024.109790
9. [9]
  Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018
10. [10]
  Jindian Duan , Xiaojuan Ding , Pui Ying Choy , Binyan Xu , Luchao Li , Hong Qin , Zheng Fang , Fuk Yee Kwong , Kai Guo . Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway. Chinese Chemical Letters, 2024, 35(10): 109565-. doi: 10.1016/j.cclet.2024.109565
11. [11]
  Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
12. [12]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
13. [13]
  Weiping Xiao , Yuhang Chen , Qin Zhao , Danil Bukhvalov , Caiqin Wang , Xiaofei Yang . Constructing the synergistic active sites of nickel bicarbonate supported Pt hierarchical nanostructure for efficient hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(12): 110176-. doi: 10.1016/j.cclet.2024.110176
14. [14]
  Qiang Wu , Baofeng Wang . Exploring synthetic strategy for stabilizing nickel-rich layered oxide cathodes through structural design. Chinese Chemical Letters, 2024, 35(12): 110089-. doi: 10.1016/j.cclet.2024.110089
15. [15]
  Jumei Zhang , Ziheng Zhang , Gang Li , Hongjin Qiao , Hua Xie , Ling Jiang . Ligand-mediated reactivity in CO oxidation of yttrium-nickel monoxide carbonyl complexes. Chinese Chemical Letters, 2025, 36(2): 110278-. doi: 10.1016/j.cclet.2024.110278
16. [16]
  Fan Chen , Xiaoyu Zhao , Weihang Miao , Yingying Li , Ye Yuan , Lingling Chu . Regio- and enantioselective hydrofluorination of internal alkenes via nickel-catalyzed hydrogen atom transfer. Chinese Chemical Letters, 2025, 36(5): 110239-. doi: 10.1016/j.cclet.2024.110239
17. [17]
  Hui Yang , Guangxun Zhang , Yueyao Sun , Huijie Zhou , Huan Pang . Bimetallic zeolitic imidazolate framework derived hollow layered double hydroxide with tailorable interlayer spacing for nickel-zinc batteries. Chinese Chemical Letters, 2025, 36(6): 110016-. doi: 10.1016/j.cclet.2024.110016
18. [18]
  Jing-Qi Tao , Shuai Liu , Tian-Yu Zhang , Hong Xin , Xu Yang , Xin-Hua Duan , Li-Na Guo . Photoinduced copper-catalyzed alkoxyl radical-triggered ring-expansion/aminocarbonylation cascade. Chinese Chemical Letters, 2024, 35(6): 109263-. doi: 10.1016/j.cclet.2023.109263
19. [19]
  Wei Zhou , Xi Chen , Lin Lu , Xian-Rong Song , Mu-Jia Luo , Qiang Xiao . Recent advances in electrocatalytic generation of indole-derived radical cations and their applications in organic synthesis. Chinese Chemical Letters, 2024, 35(4): 108902-. doi: 10.1016/j.cclet.2023.108902
20. [20]
  Yu-Yu Tan , Lin-Heng He , Wei-Min He . Copper-mediated assembly of SO₂F group via radical fluorine-atom transfer strategy. Chinese Chemical Letters, 2024, 35(9): 109986-. doi: 10.1016/j.cclet.2024.109986

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(512)
HTML views(7)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Nickel-catalyzed reductive formylation of aryl halides via formyl radical

References

Metrics

通讯作者: 陈斌, bchen63@163.com