Citation: Tian-Zhang Wang, Le-Yu Tang, Yu-Qiu Guan, Lingfei Hu, Gang Lu, Yu-Feng Liang. Nickel-catalyzed reductive alkynylation of ketoimines via unstrained C–C bond activation[J]. Chinese Chemical Letters, ;2025, 36(11): 111050. doi: 10.1016/j.cclet.2025.111050 shu

Nickel-catalyzed reductive alkynylation of ketoimines via unstrained C–C bond activation

Tian-Zhang Wang ^a ,
Le-Yu Tang ^{a, b} ,
Yu-Qiu Guan ^a ,
Lingfei Hu ^a ,
Gang Lu ^{a, *,} ,
Yu-Feng Liang ^{a, *,}

a.
School of Chemistry and Chemical Engineering, Shandong University, Ji'nan 250100, China
b.
Institut Parisien de Chimie Moléculaire, CNRS UMR 8232, Université Pierre et Marie Curie-Sorboone Universite, Paris 75005, France

ganglu@sdu.edu.cn

yfliang@sdu.edu.cn

Received Date: 24 November 2024
Revised Date: 6 March 2025
Accepted Date: 6 March 2025
Available Online: 8 March 2025

Figures(6)

The carbon–carbon bond is the one of the most fundamental and abundant bonds that exist in organic molecules, and the challenge of functionalization of carbon–carbon bond has always been a critical pursuit in organic synthesis. In recent years, there have been a growing number of studies on the C–C bond activation. Nevertheless, the metal-catalyzed cleavage of the C–C(O) bond in unstrained ketones has remained relatively underexplored due to the strong affinity of carbonyl groups for metals. In this study, we report a nickel-catalyzed strategy for the reductive alkynylation of ketoimines via β-carbon elimination. This method involves the conversion of aryl ketones into aryl ketoimines, thus expanding the toolbox of aryl electrophiles. The use of a N-heterocyclic carbene (NHC) ligand is crucial for this catalytic transformation. This discovery leads to a cross electrophile coupling reaction characterized by its operational simplicity, unique chemo-selectivity and excellent functional group tolerance. In addition, the approach has been effectively applied to the late-stage alkynylation of diverse pharmaceuticals. Ultimately, a series of comprehensive experiments and theoretical studies were conducted to provide insights into the reaction pathway, which supports the proposed β-carbon elimination process.
- Unstrained C–C bond activation,
- β-Carbon elimination,
- Nickel catalyst,
- Cross electrophile coupling,
- Alkynylation
1. [1]
  F. Chen, T. Wang, N. Jiao, Chem. Rev. 114 (2014) 8613–8661. doi: 10.1021/cr400628s
2. [2]
  F. Song, B. Wang, Z.J. Shi, Acc. Chem. Res. 56 (2023) 2867–2886. doi: 10.1021/acs.accounts.3c00230
3. [3]
  J. Xie, H. Jin, A.S.K. Hashmi, Chem. Soc. Rev. 46 (2017) 5193–5203. doi: 10.1039/C7CS00339K
4. [4]
  H. Yang, Z. Zhou, C. Tang, F. Chen, Chin. Chem. Lett. 35 (2024) 109257. doi: 10.1016/j.cclet.2023.109257
5. [5]
  B. Eftekhari-Sis, M. Zirak, Chem. Rev. 115 (2015) 151–264. doi: 10.1021/cr5004216
6. [6]
  F. Song, B. Wang, Z. J Shi, Acc. Chem. Res. 56 (2023) 2867–2886. doi: 10.1021/acs.accounts.3c00230
7. [7]
  M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 107 (2007) 3117–3179. doi: 10.1021/cr050988l
8. [8]
  B. Yuan, D. Ding, C. Wang, ACS Catal. 12 (2022) 4261–4267. doi: 10.1021/acscatal.2c00677
9. [9]
  R. Vicente, Chem. Rev. 121 (2021) 162–226. doi: 10.1021/acs.chemrev.0c00151
10. [10]
  Y. Xue, G. Dong, Acc. Chem. Res. 55 (2022) 2341–2354. doi: 10.1021/acs.accounts.2c00400
11. [11]
  D.S. Kim, W.J. Park, C.H. Jun, Chem. Rev. 117 (2017) 8977–9015. doi: 10.1021/acs.chemrev.6b00554
12. [12]
  Y.F. Liang, N. Jiao, Acc. Chem. Res. 50 (2017) 1640–1653. doi: 10.1021/acs.accounts.7b00108
13. [13]
  H. Wang, I. Choi, T. Rogge, N. Kaplaneris, L. Ackermann, Nat. Catal. 1 (2018) 993–1001. doi: 10.1038/s41929-018-0187-1
14. [14]
  X. Cheng, A. Lei, T.S. Mei, et al., CCS Chem. 4 (2022) 1120–1152. doi: 10.31635/ccschem.021.202101451
15. [15]
  S.H. Shi, Y. Liang, N. Jiao, Chem. Rev. 121 (2021) 485–505. doi: 10.1021/acs.chemrev.0c00335
16. [16]
  H. Lu, T.Y. Yu, P.F. Xu, H. Wei, Chem. Rev. 121 (2021) 365–411. doi: 10.1021/acs.chemrev.0c00153
17. [17]
  Y.F. Liang, M. Bilal, L.Y. Tang, et al., Chem. Rev. 123 (2023) 12313–12370. doi: 10.1021/acs.chemrev.3c00219
18. [18]
  W. Shang, R. Shi, D. Niu, Chin. J. Chem. 41 (2023) 2217–2236. doi: 10.1002/cjoc.202300153
19. [19]
  N.R. Candeias, R. Paterna, P.M.P. Gois, Chem. Rev. 116 (2016) 2937–2981. doi: 10.1021/acs.chemrev.5b00381
20. [20]
  J. Zhou, G. Xu, Y. Ni, ACS Catal. 10 (2020) 10954–10966. doi: 10.1021/acscatal.0c02646
21. [21]
  Y. Xu, X. Qi, P. Zheng, et al., Nature 567 (2019) 373–378. doi: 10.1038/s41586-019-0926-8
22. [22]
  J. Cao, H. Wu, Q. Wang, J. Zhu, Nat. Chem. 13 (2021) 671–676. doi: 10.1038/s41557-021-00698-y
23. [23]
  F. Song, T. Gou, B.Q. Wang, Z.J. Shi, Chem. Soc. Rev. 47 (2018) 7078–7115. doi: 10.1039/c8cs00253c
24. [24]
  Z.Q. Lei, H. Li, Y. Li, et al., Angew. Chem. Int. Ed. 51 (2012) 2690–2694. doi: 10.1002/anie.201107136
25. [25]
  Z.Q. Lei, F. Pan, H. Li, et al., J. Am. Chem. Soc. 137 (2015) 5012–5020. doi: 10.1021/ja512003d
26. [26]
  A. Dermenci, R.E. Whittaker, G. Dong, Org. Lett. 15 (2013) 2242–2245. doi: 10.1021/ol400815y
27. [27]
  A. Dermenci, R.E. Whittaker, Y. Gao, et al., Chem. Sci. 6 (2015) 3201–3210. doi: 10.1039/C5SC00584A
28. [28]
  R. Somerville, R. Martin, Angew. Chem. Int. Ed. 56 (2017) 6708–6710. doi: 10.1002/anie.201702188
29. [29]
  T. Morioka, A. Nishizawa, T. Furukawa, M. Tobisu, N. Chatani, J. Am. Chem. Soc. 139 (2017) 1416–1419. doi: 10.1021/jacs.6b12293
30. [30]
  T.T. Zhao, W.H. Xu, Z.J. Zheng, P.F. Xu, H. Wei, J. Am. Chem. Soc. 140 (2018) 586–589. doi: 10.1021/jacs.7b11591
31. [31]
  J.H. Guo, Y. Liu, X.C. Lin, et al., Angew. Chem. Int. Ed. 60 (2021) 19079–19084. doi: 10.1002/anie.202106709
32. [32]
  M.E. O'Reilly, S. Dutta, A.S. Veige, Chem. Rev. 116 (2016) 8105–8145. doi: 10.1021/acs.chemrev.6b00054
33. [33]
  M.D.R. Lutz, D. Morandi, Chem. Rev. 121 (2021) 300–326. doi: 10.1021/acs.chemrev.0c00154
34. [34]
  A.A. Tabolin, S.L. Ioffe, Chem. Rev. 114 (2014) 5426–5476. doi: 10.1021/cr400196x
35. [35]
  H. Huang, X. Ji, W. Wu, H. Jiang, Chem. Soc. Rev. 44 (2015) 1155–1171. doi: 10.1039/C4CS00288A
36. [36]
  D.D. Dong, J.C. Song, S.H. Yang, et al., Chin. Chem. Lett. 33 (2022) 1199–1206. doi: 10.1016/j.cclet.2021.08.067
37. [37]
  B. Zhao, Z. Shi, Angew. Chem. Int. Ed. 56 (2017) 12727–12731. doi: 10.1002/anie.201707181
38. [38]
  D. Ding, C. Wang, ACS Catal. 8 (2018) 11324–11329. doi: 10.1021/acscatal.8b03930
39. [39]
  W. Ai, Y. Liu, Q. Wang, Z. Lu, Q. Liu, Org. Lett. 20 (2018) 409–412. doi: 10.1021/acs.orglett.7b03707
40. [40]
  S. Cui, X. Wu, W. Ma, et al., Green Syn. Cataly. 2 (2021) 307–310.
41. [41]
  Z. Li, R.O. Torres-Ochoa, Q. Wang, J. Zhu, Nat. Commun. 11 (2020) 403–409. doi: 10.1038/s41467-020-14292-2
42. [42]
  P.Z. Wang, Y. Gao, J. Chen, et al., Nat. Commun. 12 (2021) 1815–1825. doi: 10.1038/s41467-021-22127-x
43. [43]
  C.H. Jun, H. Lee, S.G. Lim, J. Am. Chem. Soc. 123 (2001) 751–752. doi: 10.1021/ja0033537
44. [44]
  Y. Xia, G. Lu, P. Liu, G. Dong, Nature 539 (2016) 546–550. doi: 10.1038/nature19849
45. [45]
  R. Zhang, T. Yu, G. Dong, Science 382 (2023) 951–957. doi: 10.1126/science.adk1001
46. [46]
  H. Li, B. Ma, Q.S. Liu, et al., Angew. Chem. Int. Ed. 59 (2020) 14388–14393. doi: 10.1002/anie.202006740
47. [47]
  H. Li, M.L. Wang, Y.W. Liu, et al., ACS Catal. 12 (2022) 82–88. doi: 10.1021/acscatal.1c04010
48. [48]
  Z.Y. Wang, X. Zhang, W.Q. Chen, et al., Angew. Chem. Int. Ed. 63 (2024) e202319773. doi: 10.1002/anie.202319773
49. [49]
  D.J. Weix, Acc. Chem. Res. 48 (2015) 1767–1775. doi: 10.1021/acs.accounts.5b00057
50. [50]
  J. Liu, Y. Ye, J.L. Sessler, H. Gong, Acc. Chem. Res. 53 (2020) 1833–1845. doi: 10.1021/acs.accounts.0c00291
51. [51]
  X. Pang, P.F. Su, X.Z. Shu, Acc. Chem. Res. 55 (2022) 2491–2509. doi: 10.1021/acs.accounts.2c00381
52. [52]
  Q. Pan, Y. Ping, W. Kong, Acc. Chem. Res. 56 (2023) 515–535. doi: 10.1021/acs.accounts.2c00771
53. [53]
  G. Li, T. Wang, F. Fei, et al., Angew. Chem. Int. Ed. 55 (2016) 3491–3495. doi: 10.1002/anie.201511321
54. [54]
  Z. Li, K.F. Wang, X. Zhao, et al., Nat. Commun. 11 (2020) 5036–5047. doi: 10.1038/s41467-020-18834-6
55. [55]
  Y. Dai, F. Wang, S. Zhu, L. Chu, Chin. Chem. Lett. 33 (2022) 4074–4078. doi: 10.1016/j.cclet.2021.12.050
56. [56]
  Q.Q. Pan, L. Qi, X. Pang, X.Z. Shu, Angew. Chem. Int. Ed. 62 (2023) e202215703. doi: 10.1002/anie.202215703
57. [57]
  L. Xi, L. Du, Z. Shi, Chin. Chem. Lett. 33 (2022) 4287–4292. doi: 10.1016/j.cclet.2022.01.077
58. [58]
  Y.Z. Li, N. Rao, L. An, et al., Nat. Commun. 13 (2022) 5539. doi: 10.1038/s41467-022-33159-2
59. [59]
  Q. Lin, G. Ma, H. Gong, ACS Catal. 11 (2021) 14102–14109. doi: 10.1021/acscatal.1c04239
60. [60]
  L. Qi, X. Pang, K. Yin, et al., Chin. Chem. Lett. 33 (2022) 5061–5064. doi: 10.1016/j.cclet.2022.03.070
61. [61]
  Y. Li, Y. Li, H. Shi, et al., Science 376 (2022) 749–753. doi: 10.1126/science.abn9124
62. [62]
  Y. Gong, L. Su, Z. Zhu, Y. Ye, H. Gong, Angew. Chem. Int. Ed. 61 (2022) e202201662. doi: 10.1002/anie.202201662
63. [63]
  X. Wu, A. Turlik, B. Luan, et al., Angew. Chem. Int. Ed. 61 (2022) e202207536. doi: 10.1002/anie.202207536
64. [64]
  J. Lu, Y. Yao, L. Li, N. Fu, J. Am. Chem. Soc. 145 (2023) 26774–26782. doi: 10.1021/jacs.3c08839
65. [65]
  W. Du, Q. Luo, Z. Wei, et al., Sci. China Chem. 66 (2023) 2785–2790. doi: 10.1007/s11426-023-1791-3
66. [66]
  Y. Wang, Y. Ping, W. Kong, Chin. Chem. Lett. 34 (2023) 108453. doi: 10.1016/j.cclet.2023.108453
67. [67]
  Q.Q. Pan, L. Qi, X. Pang, X.Z. Shu, Angew. Chem. Int. Ed. 62 (2023) e202215703. doi: 10.1002/anie.202215703
68. [68]
  X. Ying, Y. Li, L. Li, C. Li, Angew. Chem. Int. Ed. 62 (2023) e202304177. doi: 10.1002/anie.202304177
69. [69]
  J. Yang, Z. Gui, Y. He, S. Zhu, Angew. Chem. Int. Ed. 62 (2023) e202304713. doi: 10.1002/anie.202304713
70. [70]
  L. Cheng, J. Liu, Y. Chen, H. Gong, Nat. Synth. 2 (2023) 364–372. doi: 10.1038/s44160-023-00239-0
71. [71]
  Y.C. Luo, M.K. Wang, L.C. Yu, X. Zhang, Angew. Chem. Int. Ed. 62 (2023) e202308690. doi: 10.1002/anie.202308690
72. [72]
  L. Wan, Y. Tong, X. Lu, Y. Fu, Chin. Chem. Lett. 35 (2024) 109283. doi: 10.1016/j.cclet.2023.109283
73. [73]
  Q. Pan, K. Wang, W. Xu, et al., J. Am. Chem. Soc. 146 (2024) 15453–15463. doi: 10.1021/jacs.4c03745
74. [74]
  Y.P. Shao, Z.M. Chi, Y.M. Liang, Sci. China Chem. 67 (2024) 1935–1940. doi: 10.1007/s11426-024-1949-1
75. [75]
  P. Li, Z. Zhu, C. Guo, et al., Nat. Catal. 7 (2024) 412–421. doi: 10.1038/s41929-024-01118-3
76. [76]
  S.C. Wang, L. Liu, M. Duan, et al., J. Am. Chem. Soc. 146 (2024) 30626–30636. doi: 10.1021/jacs.4c12324
77. [77]
  D. Zeng, Z. Liu, G. Huang, Y. Wang, S. Zhu, Nat. Commun. 15 (2024) 7645. doi: 10.1038/s41467-024-52054-6
78. [78]
  D. Sun, Y. Gong, Y. Wu, Y. Chen, H. Gong, Adv. Sci. 11 (2024) 2404301. doi: 10.1002/advs.202404301
79. [79]
  F.F. Tong, Y.C. Luo, H.Y. Zhao, X.P. Fu, X. Zhang, Angew. Chem. Int. Ed. 63 (2024) e202417858.
80. [80]
  J. Zhou, Y. He, Z. Liu, Y. Wang, S. Zhu, Adv. Sci. 11 (2024) 2306447. doi: 10.1002/advs.202306447
81. [81]
  X.W. Chen, C. Li, Y.Y. Gui, et al., Angew. Chem. Int. Ed. 63 (2024) e202403401. doi: 10.1002/anie.202403401
82. [82]
  S. Lu, Z. Hu, D. Wang, T. XU, Angew. Chem. Int. Ed. 63 (2024) e202406064. doi: 10.1002/anie.202406064
83. [83]
  L. Ding, M. Wang, Y. Liu, et al., Angew. Chem. Int. Ed. 63 (2024) e202413557.
84. [84]
  G.Y. Han, P.F. Su, Q.Q. Pan, X.Y. Liu, X.Z. Shu, Nat. Catal. 7 (2024) 12–20.
85. [85]
  T.Z. Wang, Y.Q. Guan, T.Y. Zhang, Y.F. Liang. Adv. Sci. 11 (2024) 2306923. doi: 10.1002/advs.202306923
86. [86]
  J.W. Wang, Q.W. Zhu, D. Liu, et al., Angew. Chem. Int. Ed. 63 (2024) e202413074. doi: 10.1002/anie.202413074
87. [87]
  X.B. Liu, R.M. Liu, X.D. Bao, H.J. Xu, Y.F. Liang, Chin. Chem. Lett. 35 (2024) 109783. doi: 10.1016/j.cclet.2024.109783
88. [88]
  X. Zhang, W. Su, H. Guo, et al., Angew. Chem. Int. Ed. 63 (2024) e202318613. doi: 10.1002/anie.202318613
89. [89]
  X. Luo, W. Mao, C.F. Liu, et al., Nat. Synth. 3 (2024) 633–642. doi: 10.1038/s44160-024-00492-x
90. [90]
  S. Xu, Y. Ping, M. Xu, et al., Nat. Chem. 16(2024) 2054–2065. doi: 10.1038/s41557-024-01629-3
91. [91]
  C. Yoo, S. Bhattacharya, X. Yi, et al., Science 382 (2023) 815–820. doi: 10.1126/science.ade3179
92. [92]
  X. Wang, G. Ma, Y. Peng, et al., J. Am. Chem. Soc. 140 (2018) 14490–14497. doi: 10.1021/jacs.8b09473
93. [93]
  L. Huang, L.K.G. Ackerman, K. Kang, A.M. Parsons, D.J. Weix, J. Am. Chem. Soc. 141 (2019) 10978–10983. doi: 10.1021/jacs.9b05461
94. [94]
  L.E. Ehehalt, O.M. Beleh, I.C. Priest, et al., Chem. Rev. 124 (2024) 13397–13569. doi: 10.1021/acs.chemrev.4c00524
95. [95]
  S.H. Newman-Stonebraker, T.J. Raab, H. Roshandel, A.G. Doyle, J. Am. Chem. Soc. 145 (2023) 19368–19377. doi: 10.1021/jacs.3c06233
96. [96]
  X. Mo, T.D.R. Morgan, H.T. Ang, D.G. Hall, J. Am. Chem. Soc. 140 (2018) 5264–5271. doi: 10.1021/jacs.8b01618
97. [97]
  R. Lavernhe, R.O. Torres-Ochoa, Q. Wang, J. Zhu, Angew. Chem. Int. Ed. 60 (2021) 24028–24033. doi: 10.1002/anie.202110901
98. [98]
  Y.M. Cai, X.T. Liu, L.L. Xu, M. Shang, Angew. Chem. Int. Ed. 63 (2024) e202315222. doi: 10.1002/anie.202315222
99. [99]
  C.X. Liu, P.P. Xie, F. Zhao, et al., J. Am. Chem. Soc. 145 (2023) 4765–4773. doi: 10.1021/jacs.2c13542
100. [100]
  B.E. Nadeau, D.D. Beattie, E.K.J. Lui, et al., Organometallics 42 (2023) 2326–2334. doi: 10.1021/acs.organomet.3c00199
101. [101]
  X. Ren, Y. Lu, G. Lu, Z.X. Wang, Org. Lett. 22 (2020) 2454–2459. doi: 10.1021/acs.orglett.0c00674
102. [102]
  Y.Q. Zhang, L. Hu, L. Yuwen, G. Lu, Q.W. Zhang, Nat. Catal. 6 (2023) 487–494. doi: 10.1038/s41929-023-00966-9
1. [1]
  Xinghao Cai , Chen Ma , Ying Kang , Yuqiang Ren , Xue Meng , Wei Lu , Shiming Fan , Shouxin Liu . Nickel-catalyzed C(sp²)–H alkynylation of free α-substituted benzylamines using a transient directing group. Chinese Chemical Letters, 2025, 36(10): 110901-. doi: 10.1016/j.cclet.2025.110901
2. [2]
  Pengfei Zhang , Qingxue Ma , Zhiwei Jiang , Xiaohua Xu , Zhong Jin . Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template. Chinese Chemical Letters, 2024, 35(8): 109361-. doi: 10.1016/j.cclet.2023.109361
3. [3]
  Jialin Huang , Liying Fu , Zhanyong Tang , Xiaoqiang Ma , Xingda Zhao , Depeng Zhao . Cross-coupling of trifluoromethylarenes with alkynes C(sp)-H bonds and azoles C(sp²)-H bonds via photoredox/copper dual catalysis. Chinese Chemical Letters, 2025, 36(7): 110505-. doi: 10.1016/j.cclet.2024.110505
4. [4]
  Xiangyang Ji , Yishuang Chen , Peng Zhang , Shaojia Song , Jian Liu , Weiyu Song . Boosting the first C–H bond activation of propane on rod-like V/CeO₂ catalyst by photo-assisted thermal catalysis. Chinese Chemical Letters, 2025, 36(5): 110719-. doi: 10.1016/j.cclet.2024.110719
5. [5]
  Lei Wan , Yizhou Tong , Xi Lu , Yao Fu . Cobalt-catalyzed reductive alkynylation to construct C(sp)-C(sp³) and C(sp)-C(sp²) bonds. Chinese Chemical Letters, 2024, 35(7): 109283-. doi: 10.1016/j.cclet.2023.109283
6. [6]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
7. [7]
  Baokang Geng , Xiang Chu , Li Liu , Lingling Zhang , Shuaishuai Zhang , Xiao Wang , Shuyan Song , Hongjie Zhang . High-efficiency PdNi single-atom alloy catalyst toward cross-coupling reaction. Chinese Chemical Letters, 2024, 35(7): 108924-. doi: 10.1016/j.cclet.2023.108924
8. [8]
  Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
9. [9]
  Peng Guo , Shicheng Dong , Xiang-Gui Zhang , Bing-Bin Yang , Jun Zhu , Ke-Yin Ye . Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane (9-BBN) borates. Chinese Chemical Letters, 2025, 36(4): 110052-. doi: 10.1016/j.cclet.2024.110052
10. [10]
  Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
11. [11]
  Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
12. [12]
  Huiyuan Deng , Na Zhao , Junjie You , Zhicheng Pan , Bo Xing , Yuling Ye , Bo Lai , Yuxi Wang , Tongrui Lu , Xiaonan Liu . Removal of bisphenol a through peroxymonosulfate activation with N-doped graphite carbon spheres coated cobalt nanoparticles catalyst: Synergy of nonradicals. Chinese Chemical Letters, 2025, 36(8): 110650-. doi: 10.1016/j.cclet.2024.110650
13. [13]
  Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
14. [14]
  Qijun Tang , Wenguang Tu , Yong Zhou , Zhigang Zou . High efficiency and selectivity catalyst for photocatalytic oxidative coupling of methane. Chinese Journal of Structural Chemistry, 2023, 42(12): 100170-100170. doi: 10.1016/j.cjsc.2023.100170
15. [15]
  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
16. [16]
  Peng Wang , Jianjun Wang , Ni Song , Xin Zhou , Ming Li . Radical dehydroxymethylative fluorination of aliphatic primary alcohols and diverse functionalization of α-fluoroimides via BF₃·OEt₂-catalyzed C‒F bond activation. Chinese Chemical Letters, 2025, 36(1): 109748-. doi: 10.1016/j.cclet.2024.109748
17. [17]
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沈阳化工大学材料科学与工程学院沈阳 110142