Citation: Chong-Yang Shi, Jian-Xing Gong, Zhen Li, Chao Shu, Long-Wu Ye, Qing Sun, Bo Zhou, Xin-Qi Zhu. Gold-catalyzed intermolecular amination of allyl azides with ynamides: Efficient construction of 3-azabicyclo[3.1.0] scaffold[J]. Chinese Chemical Letters, ;2025, 36(2): 109895. doi: 10.1016/j.cclet.2024.109895 shu

Gold-catalyzed intermolecular amination of allyl azides with ynamides: Efficient construction of 3-azabicyclo[3.1.0] scaffold

Chong-Yang Shi ^a ,
Jian-Xing Gong ^a ,
Zhen Li ^a ,
Chao Shu ^b ,
Long-Wu Ye ^{a, b, c, *,} ,
Qing Sun ^{d, *,} ,
Bo Zhou ^b ,
Xin-Qi Zhu ^{a, *,}

a.
College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, China
b.
Key Laboratory of Chemical Biology of Fujian Province, State Key Laboratory of Physical Chemistry of Solid Surfaces, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China
c.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
d.
Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China

longwuye@xmu.edu.cn

sunqing@nchu.edu.cn

xinqizhu@ynnu.edu.cn

Received Date: 31 January 2024
Revised Date: 8 April 2024
Accepted Date: 15 April 2024
Available Online: 16 April 2024

Figures(8)

Gold-catalyzed amination reactions based on azides via α-imino gold carbene intermediates have attracted extensive attention in the past decades because this methodology leads to the facile and efficient construction of synthetically useful N-containing molecules, especially valuable N-heterocycles. However, successful examples of intermolecular generation of α-imino gold carbenes by using azides as amination reagents are rarely explored probably due to the weak nucleophilicity of azides. Herein, we disclose an efficient gold-catalyzed intermolecular aminative cyclopropanation of ynamides with the allyl azides, enabling flexible synthesis of a wide range of valuable 3-azabicyclo[3.1.0]hex-2-ene derivatives in good to excellent yields with excellent diastereoselectivities. Importantly, this protocol represents the first use of allyl azide as an efficient amination reagent in gold-catalyzed alkyne amination reactions.
- Gold,
- Azides,
- Alkynes,
- Amination,
- Heterocycles
1. [1]
  M. Akter, K. Rupa, P. Anbarasan, Chem. Rev. 122 (2022) 13108–13205. doi: 10.1021/acs.chemrev.1c00991
2. [2]
  K. Pal, C.M.R. Volla, Chem. Rec. 21 (2021) 4032–4058. doi: 10.1002/tcr.202100238
3. [3]
  W. Li, J. Zhang, Chem. Eur. J. 26 (2020) 11931–11945. doi: 10.1002/chem.202000674
4. [4]
  Y. Jiang, R. Sun, X.Y. Tang, M. Shi, Chem. Eur. J. 22 (2016) 17910–17924. doi: 10.1002/chem.201601703
5. [5]
  M.L.H. Davies, J.S. Alford, Chem. Soc. Rev. 43 (2014) 5151–5162. doi: 10.1039/C4CS00072B
6. [6]
  B. Chattopadhyay, V. Gevorgyan, Angew. Chem. Int. Ed. 51 (2012) 862–872. doi: 10.1002/anie.201104807
7. [7]
  L.W. Ye, X.Q. Zhu, R.L. Sahani, et al., Chem. Rev. 121 (2021) 9039–9112. doi: 10.1021/acs.chemrev.0c00348
8. [8]
  T. Wang, A.S.K. Hashmi, Chem. Rev. 121 (2021) 8948–8978. doi: 10.1021/acs.chemrev.0c00811
9. [9]
  P.W. Davies, Chem. Rec. 21 (2021) 3964–3977. doi: 10.1002/tcr.202100205
10. [10]
  R.L. Sahani, L.W. Ye, R.S. Liu, Adv. Organomet. Chem. 73 (2020) 195–251.
11. [11]
  E. Aguilar, J. Santamaría, Org. Chem. Front. 6 (2019) 1513–1540. doi: 10.1039/c9qo00243j
12. [12]
  P.W. Davies, M. Garzón, Asian J. Org. Chem. 4 (2015) 694–708. doi: 10.1002/ajoc.201500170
13. [13]
  C. Li, L. Zhang, Org. Lett. 13 (2011) 1738–1741. doi: 10.1021/ol2002607
14. [14]
  P.W. Davies, A. Cremonesi, L. Dumitrescu, Angew. Chem. Int. Ed. 50 (2011) 8931–8935. doi: 10.1002/anie.201103563
15. [15]
  E. Chatzopoulou, P.W. Davies, Chem. Commun. 49 (2013) 8617–8619. doi: 10.1039/c3cc45410j
16. [16]
  M. Garzón, P.W. Davies, Org. Lett. 16 (2014) 4850–4853. doi: 10.1021/ol502346d
17. [17]
  A.D. Gillie, R.J. Reddy, P.W. Davies, Adv. Synth. Catal. 358 (2016) 226–239. doi: 10.1002/adsc.201500905
18. [18]
  X.H. Zhang, Z.Y. Geng, RSC Adv. 6 (2016) 62099–62108. doi: 10.1039/C6RA07780C
19. [19]
  M. Garzón, E.M. Arce, R.J. Reddy, P.W. Davies, Adv. Synth. Catal. 359 (2017) 1837–1843. doi: 10.1002/adsc.201700249
20. [20]
  R.J. Reddy, M.P. Ball-Jones, P.W. Davies, Chem. Int. Ed. 56 (2017) 13310–13313. doi: 10.1002/anie.201706850
21. [21]
  X. Tian, L. Song, M. Rudolph, et al., Angew. Chem. Int. Ed. 58 (2019) 3589–3593. doi: 10.1002/anie.201812002
22. [22]
  X. Tian, L. Song, M. Rudolph, et al., Org. Lett. 21 (2019) 1598–1601. doi: 10.1021/acs.orglett.9b00140
23. [23]
  X. Tian, L. Song, C. Han, C. Zhang, Y. Wu, Org. Lett. 21 (2019) 2937–2940. doi: 10.1021/acs.orglett.9b01011
24. [24]
  X. Tian, L. Song, M. Rudolph, F. Rominger, A.S.K. Hashmi, Org. Lett. 21 (2019) 4327–4330. doi: 10.1021/acs.orglett.9b01501
25. [25]
  X. Tian, L. Song, A.S.K. Hashmi, Angew. Chem. Int. Ed. 59 (2020) 12342–12346. doi: 10.1002/anie.202000146
26. [26]
  A.V. Mackenroth, P.W. Antoni, F. Rominger, M. Rudolph, A.S.K. Hashmi, Org. Lett. 25 (2023) 2907–2912. doi: 10.1021/acs.orglett.3c00953
27. [27]
  Q. Sun, C. Hüßler, J. Kahle, et, al., Angew. Chem. Int. Ed. 62 (2023) e202313738.
28. [28]
  A.H. Zhou, Q. He, C. Shu, et al., Chem. Sci. 6 (2015) 1265–1271. doi: 10.1039/C4SC02596B
29. [29]
  X.Y. Xiao, A.H. Zhou, C. Shu, et al., Chem. Asian J. 10 (2015)1854–1858. doi: 10.1002/asia.201500447
30. [30]
  R.L. Sahani, R.S. Liu, Angew. Chem. Int. Ed. 56 (2017) 1026–1030. doi: 10.1002/anie.201610665
31. [31]
  S.S. Giri, R.S. Liu, Chem. Sci. 9 (2018) 2991–2995. doi: 10.1039/c8sc00232k
32. [32]
  R.D. Kardile, B.S. Kale, P. Sharma, R.S. Liu, Org. Lett. 20 (2018) 3806–3809. doi: 10.1021/acs.orglett.8b01398
33. [33]
  A.S.K. Raj, K.C. Tan, L.Y. Chen, M.J. Cheng, R.S. Liu, Chem. Sci. 10 (2019) 6437–6442. doi: 10.1039/C9SC00735K
34. [34]
  Z. Tong, P.J. Smith, H.D. Pickford, K.E. Christensen, E.A. Anderson, Chem. Eur. J. 29 (2023) e202302821. doi: 10.1002/chem.202302821
35. [35]
  X.Q. Zhu, Q. Sun, Z.X. Zhang, et al., Chem. Commun. 54 (2018) 7435–7438. doi: 10.1039/c8cc03140a
36. [36]
  X.Q. Zhu, H. Yuan, Q. Sun, et al., Green Chem. 20 (2018) 4287–4291. doi: 10.1039/c8gc02051e
37. [37]
  X.Q. Zhu, Z.S. Wang, B.S. Hou, et al., Angew. Chem. Int. Ed. 59 (2020) 1666–1673. doi: 10.1002/anie.201912534
38. [38]
  H. Jin, L. Huang, J. Xie, et al., Angew. Chem. Int. Ed. 55 (2016) 794–797. doi: 10.1002/anie.201508309
39. [39]
  H. Jin, B. Tian, X. Song, et al., Angew. Chem. Int. Ed. 55 (2016) 12688–12692. doi: 10.1002/anie.201606043
40. [40]
  R.L. Sahani, R.S. Liu, Angew. Chem. Int. Ed. 56 (2017) 12736–12740. doi: 10.1002/anie.201707423
41. [41]
  Z. Zeng, H. Jin, K. Sekine, et al., Angew. Chem. Int. Ed. 57 (2018) 6935–6939. doi: 10.1002/anie.201802445
42. [42]
  Z. Zeng, H. Jin, M. Rudolph, F. Rominger, A.S.K. Hashmi, Angew. Chem. Int. Ed. 57 (2018) 16549–16553. doi: 10.1002/anie.201810369
43. [43]
  B.D. Mokar, P.D. Jadhav, Y.B. Pandit, R.S. Liu, Chem. Sci. 9 (2018) 4488–4492. doi: 10.1039/c8sc00986d
44. [44]
  R.R. Singh, M. Skaria, L.Y. Chen, M.J. Cheng, R.S. Liu, Chem. Sci. 10 (2019) 1201–1206. doi: 10.1039/c8sc03619e
45. [45]
  L. Song, X. Tian, M. Rudolph, F. Romingera, A.S.K. Hashmi, Chem. Commun. 55 (2019) 9007–9010. doi: 10.1039/c9cc04027g
46. [46]
  X. Tian, L. Song, K. Farshadfar, et al., Angew. Chem. Int. Ed. 59 (2020) 471–478. doi: 10.1002/anie.201912334
47. [47]
  A. Prechter, G. Henrion, P.F. dit Bel, F. Gagosz, Angew. Chem. Int. Ed. 53 (2014) 4959–4963. doi: 10.1002/anie.201402470
48. [48]
  L. Zhu, Y. Yu, Z. Mao, X. Huang, Org. Lett. 17 (2015) 30–33. doi: 10.1021/ol503172h
49. [49]
  S.K. Pawar, R.L. Sahani, R.S. Liu, Chem. Eur. J. 21 (2015) 10843–10850. doi: 10.1002/chem.201500694
50. [50]
  Z. Zeng, H. Jin, J. Xie, et al., Org. Lett. 19 (2017) 1020–1023. doi: 10.1021/acs.orglett.7b00001
51. [51]
  W. Xu, G. Wang, N. Sun, Y. Liu, Org. Lett. 19 (2017) 3307–3310. doi: 10.1021/acs.orglett.7b01469
52. [52]
  W. Xu, Y. Chen, A. Wang, Y. Liu, Org. Lett. 21 (2019) 7613–7618. doi: 10.1021/acs.orglett.9b02893
53. [53]
  D.J. Gorin, N.R. Davis, F.D. Toste, J. Am. Chem. Soc. 127 (2005) 11260–11261. doi: 10.1021/ja053804t
54. [54]
  C.A. Witham, P. Mauleón, N.D. Shapiro, B.D. Sherry, F.D. Toste, J. Am. Chem. Soc. 129 (2007) 5838–5839. doi: 10.1021/ja071231+
55. [55]
  A. Wetzel, F. Gagosz, Angew. Chem., Int. Ed. 50 (2011) 7354–7358. doi: 10.1002/anie.201102707
56. [56]
  B. Lu, Y. Luo, L. Liu, et al., Angew. Chem. Int. Ed. 50 (2011) 8358–8362. doi: 10.1002/anie.201103014
57. [57]
  J. Matsuoka, Y. Matsuda, Y. Kawada, S. Oishi, H. Ohno, Angew. Chem. Int. Ed. 56 (2017) 7444–7448. doi: 10.1002/anie.201703279
58. [58]
  W.B. Shen, Q. Sun, L. Li, et al., Nat. Commun. 8 (2017)1748. doi: 10.1038/s41467-017-01853-1
59. [59]
  J.M. Xie, Y.L. Zhu, Y.M. Fu, et al., Org. Lett. 25 (2023) 421–425. doi: 10.1021/acs.orglett.2c04147
60. [60]
  S.P. Sancheti, D.J. Mondal, N.T. Patil, ACS Catal. 13 (2023) 4391–4397. doi: 10.1021/acscatal.3c00088
61. [61]
  D.F.L. Rayo, A. Mansour, W. Wu, B.N. Bhawal, F. Gagosz, Angew. Chem. Int. Ed. 62 (2023) e202212893. doi: 10.1002/anie.202212893
62. [62]
  L.C. Greiner, N. Arichi, S. Inuki, H. Ohno, Angew. Chem. Int. Ed. 62 (2023) e202213653. doi: 10.1002/anie.202213653
63. [63]
  X. Liu, Z.S. Wang, T.Y. Zhai, et al., Angew. Chem. Int. Ed. 59 (2020) 17984–17990. doi: 10.1002/anie.202007206
64. [64]
  C.Y. Weng, G.Y. Zhu, B.H. Zhu, et al., Org. Chem. Front. 9 (2022) 2773–2778. doi: 10.1039/d2qo00457g
65. [65]
  X. Liu, L.G. Liu, C.M. Chen, et al., Angew. Chem. Int. Ed. 62 (2023) e202216923. doi: 10.1002/anie.202216923
66. [66]
  Y. Chen, Y.H. Yan, B.H. Zhu, et al., Org. Lett. 25 (2023) 2063–2067. doi: 10.1021/acs.orglett.3c00434
67. [67]
  D. Huang, G. Yan, Adv. Synth. Catal. 359 (2017) 1600–1619. doi: 10.1002/adsc.201700103
68. [68]
  X.R. Song, Y.F. Qiu, X.Y. Liu, Y.M. Liang, Org. Biomol. Chem. 14 (2016) 11317–11331. doi: 10.1039/C6OB01965J
69. [69]
  C. Shu, Y.H. Wang, B. Zhou, et al., J. Am. Chem. Soc. 137 (2015) 9567–9570. doi: 10.1021/jacs.5b06015
70. [70]
  B. Zhou, Y.Q. Zhang, X. Liu, L.W. Ye, Sci. Bull. 62 (2017) 1201–1206. doi: 10.1016/j.scib.2017.08.020
71. [71]
  C. Shu, Y.H. Wang, C.H. Shen, et al., Org. Lett. 18 (2016) 3254–3257. doi: 10.1021/acs.orglett.6b01503
72. [72]
  C. Shu, C.H. Shen, Y.H. Wang, et al., Org. Lett. 18 (2016) 4630–4633. doi: 10.1021/acs.orglett.6b02267
73. [73]
  Y.C. Hu, Y. Zhao, B. Wan, Q.A. Chen, Chem. Soc. Rev. 50 (2021) 2582–2625. doi: 10.1039/d0cs00283f
74. [74]
  C.C. Lynch, A. Sripada, C. Wolf, Chem. Soc. Rev. 49 (2020) 8543–8583. doi: 10.1039/d0cs00769b
75. [75]
  Y.B. Chen, P.C. Qian, L.W. Ye, Chem. Soc. Rev. 49 (2020) 8897–8909. doi: 10.1039/d0cs00474j
76. [76]
  F.L. Hong, L.W. Ye, Acc. Chem. Res. 53 (2020) 2003–2019. doi: 10.1021/acs.accounts.0c00417
77. [77]
  B. Zhou, T.D. Tan, X.Q. Zhu, M. Shang, L.W. Ye, ACS Catal. 9 (2019) 6393–6406. doi: 10.1021/acscatal.9b01851
78. [78]
  G. Evano, C. Theunissen, M. Lecomte, Aldrichimica Acta 48 (2015) 59–77.
79. [79]
  X.N. Wang, H.S. Yeom, L.C. Fang, et al., Acc. Chem. Res. 47 (2014) 560–578. doi: 10.1021/ar400193g
80. [80]
  Y.B. Chen, L.G. Liu, C.M. Chen, et al., Angew. Chem. Int. Ed. 62 (2023) e202303670. doi: 10.1002/anie.202303670
81. [81]
  C.T. Li, L.J. Qi, L.G. Liu, et al., Nat. Commun. 14(2023)7058. doi: 10.1038/s41467-023-42805-2
82. [82]
  Y. Xu, G.L. Qian, D.Q. Cui, et al., ACS Catal. 13(2023) 8803–8812. doi: 10.1021/acscatal.3c01680
83. [83]
  Z.X. Zhang, L.G. Liu, Y.X. Liu, et al., Chem. Sci. 14 (2023) 5918–5924. doi: 10.1039/d3sc01880f
84. [84]
  Z.X. Zhang, X. Wang, J.T. Jiang, et al., Chin. Chem. Lett. 34 (2023) 107647. doi: 10.1016/j.cclet.2022.06.070
85. [85]
  L.J. Qi, C.T. Li, Z.Q. Huang, et al., Angew. Chem. Int. Ed. 61 (2022) e202210637. doi: 10.1002/anie.202210637
86. [86]
  G.Y. Zhu, J.J. Zhou, L.G. Liu, et al., Angew. Chem. Int. Ed. 61 (2022) e202204603. doi: 10.1002/anie.202204603
87. [87]
  Z.S. Wang, L.J. Zhu, C.T. Li, et al., Angew. Chem. Int. Ed. 61 (2022) e.202201436. doi: 10.1002/anie.202201436
88. [88]
  F.L. Hong, C.Y. Shi, P. Hong, et al., Angew. Chem. Int. Ed. 61 (2022) e202115554. doi: 10.1002/anie.202115554
89. [89]
  Y.Q. Zhang, Y.B. Chen, J.R. Liu, et al., Nat. Chem. 13 (2021) 1093–1100. doi: 10.1038/s41557-021-00778-z
90. [90]
  P.F. Chen, B. Zhou, P. Wu, B. Wang, L.W. Ye, Angew. Chem. Int. Ed. 60 (2021) 27164–27170. doi: 10.1002/anie.202113464
91. [91]
  X.Q. Zhu, P. Hong, Y.X. Zheng, et al., Chem. Sci. 12 (2021) 9466–9474. doi: 10.1039/d1sc02773e
92. [92]
  D.L. Boger, C.W. Boyce, R.M. Garbaccio, Chem. Rev. 97 (1997) 787–828. doi: 10.1021/cr960095g
93. [93]
  F.G. Njoroge, K.X. Chen, N.Y. Shih, J. Piwinski, Acc. Chem. Res. 41 (2008) 50–59. doi: 10.1021/ar700109k
94. [94]
  J.W. Epstein, H.J. Brabander, W.J. Fanshawe, et al., J. Med. Chem. 24 (1981) 481–490. doi: 10.1021/jm00137a002
95. [95]
  G. Kim, M.Y. Chu-Moyer, S.J. Danishefsky, J. Am. Chem. Soc. 112 (1990) 2003–2005. doi: 10.1021/ja00161a059
96. [96]
  D.L. Boger, W. Yun, S. Terashima, et al., Med. Chem. Lett. 7 (1992) 759–765.
97. [97]
  E.W. Hook 3rd, G.B. Pinson, C.J. Blalock, R.B. Johnson, Antimicrob. Agents Chemother. 40 (1996) 1720–1721. doi: 10.1128/AAC.40.7.1720
98. [98]
  L.A. Sorbera, J. Castaner, P.A. Leeson, Drugs Fut. 30 (2005) 7–10. doi: 10.1358/dof.2005.030.01.871476
99. [99]
  M. Zhang, F. Jovic, T. Vickers, et al., Bioorg. Med. Chem. Lett. 18 (2008) 3682–3686. doi: 10.1016/j.bmcl.2008.05.077
100. [100]
  J. Pedroni, N. Cramer, J. Am. Chem. Soc. 139 (2017) 12398–12401. doi: 10.1021/jacs.7b07024
101. [101]
  L. Fu, F. Ye, Y. Feng, et al., Nat. Commun. 11 (2020) 4417. doi: 10.1038/s41467-020-18233-x
102. [102]
  Y. Liao, Q. Lu, G. Chen, et al., ACS Catal. 7 (2017) 7529–7534. doi: 10.1021/acscatal.7b02558
103. [103]
  P. Destito, J.R. Couceiro, H. Faustino, F. López, J.L. Mascareñas, Angew. Chem. Int. Ed. 56 (2017) 10766–10770. doi: 10.1002/anie.201705006
104. [104]
  B.C. Boren, S. Narayan, L.K. Rasmussen, et al., J. Am. Chem. Soc. 130 (2008) 8923–8930. doi: 10.1021/ja0749993
105. [105]
  L. Zhang, X. Chen, P. Xue, et al., J. Am. Chem. Soc. 127 (2005) 15998–15999. doi: 10.1021/ja054114s
106. [106]
  J. Caruano, G.G. Mucciolib, R. Robiette, Org. Biomol. Chem. 14 (2016) 10134–10156. doi: 10.1039/C6OB01349J
107. [107]
  L.W. Ye, C. Shu, F. Gagosz, Org. Biomol. Chem. 12 (2014) 1833–1845. doi: 10.1039/C3OB42181C
108. [108]
  A. Albrecht, Ł. Albrecht, T. Janecki, Eur. J. Org. Chem. 2011 (2011) 2747–2766. doi: 10.1002/ejoc.201001486
109. [109]
  L.X. Ruan, B. Sun, J.M. Liu, S.L. Shi, Science 379 (2023) 662–670. doi: 10.1126/science.ade0760
110. [110]
  Z.C. Wan, X. Luo, J.W. Zhang, et al., Nat. Catal. 6 (2023) 1087–1097. doi: 10.1038/s41929-023-01037-9
111. [111]
  Z.C. Wang, J.W. Zhang, M.J. Koh, S.L. Shi, Angew. Chem. Int. Ed. 62 (2023) e202310203. doi: 10.1002/anie.202310203
112. [112]
  J.B. Ma, X. Zhao, D. Zhang, S.L. Shi, J. Am. Chem. Soc. 144 (2022) 13643–13651. doi: 10.1021/jacs.2c04043
113. [113]
  Y. Cai, S.L. Shi, J. Am. Chem. Soc. 143 (2021) 11963–11968. doi: 10.1021/jacs.1c06614
114. [114]
  Z.C. Wang, P.P. Xie, Y. Xu, X. Hong, S.L. Shi, Angew. Chem. Int. Ed. 60 (2021)16077–16084. doi: 10.1002/anie.202103803
115. [115]
  Y. Cai, J.W. Zhang, F. Li, J.M. Liu, S.L. Shi, ACS Catal. 9 (2019) 1–6. doi: 10.1021/acscatal.8b04198
1. [1]
  Wen-Tao Ouyang , Jun Jiang , Yan-Fang Jiang , Ting Li , Yuan-Yuan Liu , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038
2. [2]
  Wen-Jing Li , Jun-Bo Wang , Yu-Heng Liu , Mo Zhang , Zhan-Hui Zhang . Molybdenum-doped carbon nitride as an efficient heterogeneous catalyst for direct amination of nitroarenes with arylboronic acids. Chinese Chemical Letters, 2025, 36(3): 110001-. doi: 10.1016/j.cclet.2024.110001
3. [3]
  Heng Yang , Zhijie Zhou , Conghui Tang , Feng Chen . Recent advances in heterogeneous hydrosilylation of unsaturated carbon-carbon bonds. Chinese Chemical Letters, 2024, 35(6): 109257-. doi: 10.1016/j.cclet.2023.109257
4. [4]
  Boqiang Wang , Yongzhuo Xu , Jiajia Wang , Muyang Yang , Guo-Jun Deng , Wen Shao . Transition-metal free trifluoromethylimination of alkenes enabled by direct activation of N-unprotected ketimines. Chinese Chemical Letters, 2024, 35(9): 109502-. doi: 10.1016/j.cclet.2024.109502
5. [5]
  Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
6. [6]
  Pengcheng Su , Shizheng Chen , Zhihong Yang , Ningning Zhong , Chenzi Jiang , Wanbin Li . Vapor-phase postsynthetic amination of hypercrosslinked polymers for efficient iodine capture. Chinese Chemical Letters, 2024, 35(9): 109357-. doi: 10.1016/j.cclet.2023.109357
7. [7]
  Shaonan Tian , Yu Zhang , Qing Zeng , Junyu Zhong , Hui Liu , Lin Xu , Jun Yang . Core-shell gold-copper nanoparticles: Evolution of copper shells on gold cores at different gold/copper precursor ratios. Chinese Journal of Structural Chemistry, 2023, 42(11): 100160-100160. doi: 10.1016/j.cjsc.2023.100160
8. [8]
  Zhi Li , Wenpei Li , Shaoping Jiang , Chuan Hu , Yuanyu Huang , Maxim Shevtsov , Huile Gao , Shaobo Ruan . Legumain-triggered aggregable gold nanoparticles for enhanced intratumoral retention. Chinese Chemical Letters, 2024, 35(7): 109150-. doi: 10.1016/j.cclet.2023.109150
9. [9]
  Xiangqian Cao , Chenkai Yang , Xiaodong Zhu , Mengxin Zhao , Yilin Yan , Zhengnan Huang , Jinming Cai , Jingming Zhuang , Shengzhou Li , Wei Li , Bing Shen . Synergistic enhancement of chemotherapy for bladder cancer by photothermal dual-sensitive nanosystem with gold nanoparticles and PNIPAM. Chinese Chemical Letters, 2024, 35(8): 109199-. doi: 10.1016/j.cclet.2023.109199
10. [10]
  Min Huang , Ru Cheng , Shuai Wen , Liangtong Li , Jie Gao , Xiaohui Zhao , Chunmei Li , Hongyan Zou , Jian Wang . Ultrasensitive detection of microRNA-21 in human serum based on the confinement effect enhanced chemical etching of gold nanorods. Chinese Chemical Letters, 2024, 35(9): 109379-. doi: 10.1016/j.cclet.2023.109379
11. [11]
  Ji Liu , Dongsheng He , Tianjiao Hao , Yumin Hu , Yan Zhao , Zhen Li , Chang Liu , Daquan Chen , Qiyue Wang , Xiaofei Xin , Yan Shen . Gold mineralized "hybrid nanozyme bomb" for NIR-II triggered tumor effective permeation and cocktail therapy. Chinese Chemical Letters, 2024, 35(9): 109296-. doi: 10.1016/j.cclet.2023.109296
12. [12]
  Ya-Wen Zhang , Ming-Ming Gan , Li-Ying Sun , Ying-Feng Han . Supramolecular dinuclear silver(I) and gold(I) tetracarbene metallacycles and fluorescence sensing of penicillamine. Chinese Journal of Structural Chemistry, 2024, 43(9): 100356-100356. doi: 10.1016/j.cjsc.2024.100356
13. [13]
  Hao Zhang , Haonan Qu , Ehsan Bahojb Noruzi , Haibing Li , Feng Liang . A nanocomposite film with layer-by-layer self-assembled gold nanospheres driven by cucurbit[7]uril for the selective transport of L-tryptophan and lysozyme. Chinese Chemical Letters, 2025, 36(1): 109731-. doi: 10.1016/j.cclet.2024.109731
14. [14]
  Xiangdong Lai , Tengfei Liu , Zengchao Guo , Yihan Wang , Jiang Xiao , Qingxiu Xia , Xiaohui Liu , Hui Jiang , Xuemei Wang . In situ formed fluorescent gold nanoclusters inhibit hair follicle regeneration in oxidative stress microenvironment via suppressing NFκB signal pathway. Chinese Chemical Letters, 2025, 36(2): 109762-. doi: 10.1016/j.cclet.2024.109762

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(203)
HTML views(12)

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