Citation: Zhi-Xin Zhang, Xuan Wang, Jia-Tian Jiang, Jie Chen, Xin-Qi Zhu, Long-Wu Ye. Brønsted acid-catalyzed asymmetric dearomatization of indolyl ynamides: Practical and enantioselective synthesis of polycyclic indolines[J]. Chinese Chemical Letters, ;2023, 34(3): 107647. doi: 10.1016/j.cclet.2022.06.070 shu

Brønsted acid-catalyzed asymmetric dearomatization of indolyl ynamides: Practical and enantioselective synthesis of polycyclic indolines

Zhi-Xin Zhang ^a ,
Xuan Wang ^a ,
Jia-Tian Jiang ^a ,
Jie Chen ^a ,
Xin-Qi Zhu ^{a, *,} ,
Long-Wu Ye ^{a, b, c, *,}

a.
Key Laboratory for Chemical Biology of Fujian Province and State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China
b.
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
c.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

xinqizhu@xmu.edu.cn

longwuye@xmu.edu.cn

Received Date: 22 May 2022
Revised Date: 26 June 2022
Accepted Date: 26 June 2022
Available Online: 2 July 2022

Figures(7)

Catalytic asymmetric dearomatization of indoles and alkynes has received much attention in the past decade because this strategy offers an attractive and alternative way for the efficient synthesis of valuable chiral polycyclic indolines. However, these reactions have been mostly limited to transition-metal catalysts, and the related chiral Brønsted acid catalysis has been scarcely reported. Herein, we disclose a chiral phosphoric acid-catalyzed asymmetric dearomatization of indolyl ynamides by direct activation of alkynes. This metal-free method enables the practical and atom-economical construction of an array of valuable chiral polycyclic indolines in moderate to good yields with high enantioselectivities
- Brønsted acid catalysis,
- Dearomatization,
- Heterocycles,
- Ynamides,
- Stereoselectivity
1. [1]
  T.S. Kam, Y.M. Choo, J. Nat. Prod. 67 (2004) 547-552. doi: 10.1021/np034041v
2. [2]
  A. Ramirez, S. Garcia-Rubio, Curr. Med. Chem. 10 (2003) 1891-1915. doi: 10.2174/0929867033457016
3. [3]
  Y. Igarashi, K. Futamata, T. Fujita, et al., Antibiot. 56 (2003) 107-113. doi: 10.7164/antibiotics.56.107
4. [4]
  I. Takahashi, K. Takahashi, M. Ichimura, et al., Antibiot. 41 (1988) 1915-1917. doi: 10.7164/antibiotics.41.1915
5. [5]
  J.J. Dugan, M. Hesse, U. Renner, H. Schmid, Helv. Chim. Acta 52 (1969) 701-707. doi: 10.1002/hlca.19690520318
6. [6]
  H.K. Schnoes, K. Biemann, J. Mokry, et al., J. Org. Chem. 31 (1966) 1641-1642. doi: 10.1021/jo01343a507
7. [7]
  Y. Zhu, W. He, W. Wang, C.E. Pitsch, X. Wang, Angew. Chem. Int. Ed. 56 (2017) 12206-12209. doi: 10.1002/anie.201706694
8. [8]
  L. Jiang, Y. Yu, G. Li, L. Zu, Chem. Asian J. 11 (2016) 2838-2840. doi: 10.1002/asia.201600980
9. [9]
  R.A. Bauer, J.M. Wurst, D.S. Tan, Curr. Opin. Chem. Biol. 14 (2010) 308-314. doi: 10.1016/j.cbpa.2010.02.001
10. [10]
  C. Zheng, S.L. You, ACS Cent. Sci. 7 (2021) 432-444. doi: 10.1021/acscentsci.0c01651
11. [11]
  F.T. Sheng, J.Y. Wang, W. Tan, Y.C. Zhang, F. Shi, Org. Chem. Front. 7 (2020) 3967-3998. doi: 10.1039/d0qo01124j
12. [12]
  Z.L. Xia, Q.F. Xu, C. Zheng, S.L. You, Chem. Soc. Rev. 49 (2020) 286-300. doi: 10.1039/c8cs00436f
13. [13]
  C. Zheng, S.L. You, Nat. Prod. Rep. 36 (2019) 1589-1605. doi: 10.1039/c8np00098k
14. [14]
  G. Huang, B. Yin, Adv. Synth. Catal. 361 (2019) 405-425. doi: 10.1002/adsc.201800789
15. [15]
  W.T. Wu, L. Zhang, S.L. You, Acta Chim. Sinica 75 (2017) 419-438. doi: 10.6023/A17020049
16. [16]
  C. Zheng, S.L. You, Chem 1 (2016) 830-857. doi: 10.1016/j.chempr.2016.11.005
17. [17]
  W.T. Wu, L. Zhang, S.L. You, Chem. Soc. Rev. 45 (2016) 1570-1580. doi: 10.1039/C5CS00356C
18. [18]
  C.X. Zhuo, C. Zheng, S.L. You, Acc. Chem. Res. 47 (2014) 2558-2573. doi: 10.1021/ar500167f
19. [19]
  C.X. Zhuo, W. Zhang, S.L. You, Angew. Chem. Int. Ed. 51 (2012) 12662-12686. doi: 10.1002/anie.201204822
20. [20]
  T. Ito, S. Harada, H. Homma, et al., J. Am. Chem. Soc. 143 (2021) 604-611. doi: 10.1021/jacs.0c10682
21. [21]
  R.Q. Xu, P. Yang, C. Zheng, S.L. You, Chin. J. Chem. 38 (2020) 683-689. doi: 10.1002/cjoc.202000109
22. [22]
  X. Liu, J. Zhang, L. Bai, et al., Chem. Sci. 11 (2020) 671-676. doi: 10.1039/c9sc05320d
23. [23]
  K. Du, P. Guo, Y. Chen, et al., Angew. Chem. Int. Ed. 54 (2015) 3033-3037. doi: 10.1002/anie.201411817
24. [24]
  R.Q. Xu, Q. Gu, W.T. Wu, Z.A. Zhao, S.L. You, J. Am. Chem. Soc. 136 (2014) 15469-15472. doi: 10.1021/ja508645j
25. [25]
  Q.F. Wu, W.B. Liu, C.X. Zhuo, et al., Angew. Chem. Int. Ed. 50 (2011) 4455-4458. doi: 10.1002/anie.201100206
26. [26]
  T. Nemoto, Y. Ishige, M. Yoshida, et al., Org. Lett. 12 (2010) 5020-5023. doi: 10.1021/ol102190s
27. [27]
  R.B. Bedford, C.P. Butts, M.F. Haddow, R. Osborne, R.F. Sankey, Chem. Commun. 45 (2009) 4832-4834. doi: 10.1039/b910894g
28. [28]
  L. Bai, X. Luo, Y. Ge, et al., CCS Chem. 4 (2022) 1054-1064. doi: 10.31635/ccschem.021.202100831
29. [29]
  B. Yang, X. Zhai, S. Feng, et al., Org. Lett. 21 (2019) 330-334. doi: 10.1021/acs.orglett.8b03934
30. [30]
  X. Liu, P. Wang, L. Bai, et al., ACS Catal. 8 (2018) 10888-10894. doi: 10.1021/acscatal.8b03905
31. [31]
  Q. Cheng, Y. Wang, S.L. You, Angew. Chem. Int. Ed. 55 (2016) 3496-3499. doi: 10.1002/anie.201511519
32. [32]
  J. Zheng, S.B. Wang, C. Zheng, S.L. You, J. Am. Chem. Soc. 137 (2015) 4880-4883. doi: 10.1021/jacs.5b01707
33. [33]
  L. Yang, H. Zheng, L. Luo, et al., J. Am. Chem. Soc. 137 (2015) 4876-4879. doi: 10.1021/jacs.5b01285
34. [34]
  J. Nan, J. Liu, H. Zheng, et al., Angew. Chem. Int. Ed. 54 (2015) 2356-2360. doi: 10.1002/anie.201409565
35. [35]
  S.G. Wang, Q. Yin, C.X. Zhuo, S.L. You, Angew. Chem. Int. Ed. 54 (2015) 647-650.
36. [36]
  C.X. Zhuo, S.L. You, Angew. Chem. Int. Ed. 52 (2013) 10056-10059. doi: 10.1002/anie.201304591
37. [37]
  J. García-Fortanet, F. Kessler, S.L. Buchwald, J. Am. Chem. Soc. 131 (2009) 6676-6677. doi: 10.1021/ja9025193
38. [38]
  Q.F. Wu, C. Zheng, C.X. Zhuo, S.L. You, Chem. Sci. 7 (2016) 4453-4459. doi: 10.1039/C6SC00176A
39. [39]
  X. Zhang, W.B. Liu, H.F. Tu, S. L You, Chem. Sci. 6 (2015) 4525-4529. doi: 10.1039/C5SC01772F
40. [40]
  X. Zhang, L. Han, S.L. You, Chem. Sci. 5 (2014) 1059-1063. doi: 10.1039/c3sc53019a
41. [41]
  C.X. Zhuo, Q.F. Wu, Q. Zhao, Q.L. Xu, S.L. You, J. Am. Chem. Soc. 135 (2013) 8169-8172. doi: 10.1021/ja403535a
42. [42]
  Q.L. Xu, L.X. Dai, S.L. You, Chem. Sci. 4 (2013) 97-102. doi: 10.1039/C2SC21085A
43. [43]
  Q.F. Wu, C. Zheng, S.L. You, Angew. Chem. Int. Ed. 51 (2012) 1680-1683. doi: 10.1002/anie.201107677
44. [44]
  Q.F. Wu, H. He, W.B. Liu, S.L. You, J. Am. Chem. Soc. 132 (2010) 11418-11419. doi: 10.1021/ja105111n
45. [45]
  J. Matsuoka, H. Kumagai, S. Inuki, S. Oishi, H. Ohno, J. Org. Chem. 84 (2019) 9358-9363. doi: 10.1021/acs.joc.9b01149
46. [46]
  R. Ocello, A. De Nisi, M. Jia, et al., Chem. Eur. J. 21 (2015) 18445-18453. doi: 10.1002/chem.201503598
47. [47]
  M. Jia, M. Monari, Q.Q. Yang, M. Bandini, Chem. Commun. 51 (2015) 2320-2323. doi: 10.1039/C4CC08736D
48. [48]
  G. Cera, M. Chiarucci, A. Mazzanti, M. Mancinelli, M. Bandini, Org. Lett. 14 (2012) 1350-1353. doi: 10.1021/ol300297t
49. [49]
  C. Liu, J.C. Yi, Z.B. Zheng, et al., Angew. Chem. Int. Ed. 55 (2016) 751-754. doi: 10.1002/anie.201508570
50. [50]
  S. Zhu, D.W.C. MacMillan, J. Am. Chem. Soc. 134 (2012) 10815-10818. doi: 10.1021/ja305100g
51. [51]
  D. Gao, L. Jiao, Angew. Chem. Int. Ed. 61 (2022) e202116024.
52. [52]
  Y. Li, Y. Su, H.Y. Zhang, et al., ChemistrySelect 6 (2021) 4719-4724. doi: 10.1002/slct.202101238
53. [53]
  Z.S. Liu, W.K. Li, T.R. Kang, L. He, Q.Z. Liu, Org. Lett. 17 (2015) 150-153. doi: 10.1021/ol503383x
54. [54]
  B.M. Trost, J. Quancard, J. Am. Chem. Soc. 128 (2006) 6314-6315. doi: 10.1021/ja0608139
55. [55]
  J.Y. Wang, S. Zhang, X.Y. Yu, et al., Tetrahedron Chem. 1 (2022) 100007. doi: 10.1016/j.tchem.2022.100007
56. [56]
  S. Biswas, H. Kim, K.L.A. Cao, S. Shin, Adv. Synth. Catal. 362 (2020) 1841-1845. doi: 10.1002/adsc.202000083
57. [57]
  J. Yang, Z. Wang, Z. He, et al., Angew. Chem. Int. Ed. 59 (2020) 642-647. doi: 10.1002/anie.201911420
58. [58]
  L.W. Qi, J.H. Mao, J. Zhang, B. Tan, Nat. Chem. 10 (2018) 58-64. doi: 10.1038/nchem.2866
59. [59]
  C. Ma, T. Zhang, J.Y. Zhou, G.J. Mei, F. Shi, Chem. Commun. 53 (2017) 12124-12127. doi: 10.1039/C7CC06547G
60. [60]
  F. Jiang, D. Zhao, X. Yang, et al., ACS Catal. 7 (2017) 6984-6989. doi: 10.1021/acscatal.7b02279
61. [61]
  C. Romano, M. Jia, M. Monari, E. Manoni, M. Bandini, Angew. Chem. Int. Ed. 53 (2014) 13854-13857. doi: 10.1002/anie.201407518
62. [62]
  H.M. Nelson, S.H. Reisberg, H.P. Shunatona, J.S. Patel, F.D. Toste, Angew. Chem. Int. Ed. 53 (2014) 5600-5603. doi: 10.1002/anie.201310905
63. [63]
  D.H. Duan, Q. Yin, S.G. Wang, Q. Gu, S.L. You, Acta Chim. Sin. 72 (2014) 1001-1004. doi: 10.6023/A14060497
64. [64]
  W. Xie, G. Jiang, H. Liu, et al., Angew. Chem. Int. Ed. 52 (2013) 12924-12927. doi: 10.1002/anie.201306774
65. [65]
  Z. Zhang, J. C. Antilla, Angew. Chem. Int. Ed. 51 (2012) 11778-11782. doi: 10.1002/anie.201203553
66. [66]
  Q. Cai, C. Liu, X.W. Liang, S.L. You, Org. Lett. 14 (2012) 4588-4590. doi: 10.1021/ol302043s
67. [67]
  P.H. Dou, Y. Chen, Y. You, et al., Adv. Synth. Catal. 363 (2021) 4047-4053. doi: 10.1002/adsc.202100516
68. [68]
  K. Li, T.P. Gonçalves, K.W. Huang, Y. Lu, Angew. Chem. Int. Ed. 58 (2019) 5427-5431. doi: 10.1002/anie.201900248
69. [69]
  L. Zhao, B. Guo, G. Huang, et al., ACS Catal. 4 (2014) 4420-4424. doi: 10.1021/cs5015496
70. [70]
  Q. Cai, Q. Yin, S.L. You, Asian J. Org. Chem. 3 (2014) 408-411. doi: 10.1002/ajoc.201300146
71. [71]
  D. Enders, C. Joie, K. Deckers, Chem. Eur. J. 19 (2013) 10818-10821. doi: 10.1002/chem.201302127
72. [72]
  J. Huang, L. Zhao, Y. Liu, W. Cao, X. Wu, Org. Lett. 15 (2013) 4338-4341. doi: 10.1021/ol401809d
73. [73]
  Q. Cai, S.L. You, Org. Lett. 14 (2012) 3040-3043. doi: 10.1021/ol301114z
74. [74]
  O. Lozano, G. Blessley, T. Martinez del Campo, et al., Angew. Chem. Int. Ed. 50 (2011) 8105-8109. doi: 10.1002/anie.201103151
75. [75]
  S.B. Jones, B. Simmons, A. Mastracchio, D.W.C. MacMillan, Nature, 475 (2011) 183-188. doi: 10.1038/nature10232
76. [76]
  C. Gioia, A. Hauville, L. Bernardi, F. Fini, A. Ricci, Angew. Chem. Int. Ed. 47 (2008) 9236-9239. doi: 10.1002/anie.200804275
77. [77]
  S.B. Jones, B. Simmons, D.W.C. MacMillan, J. Am. Chem. Soc. 131 (2009) 13606-13607. doi: 10.1021/ja906472m
78. [78]
  J.F. Austin, S.G. Kim, C.J. Sinz, W.J. Xiao, D.W.C. MacMillan, Proc. Natl. Acad. Sci. U. S. A. 101 (2004) 5482-5487. doi: 10.1073/pnas.0308177101
79. [79]
  L.M. Repka, J. Ni, S.E. Reisman, J. Am. Chem. Soc. 132 (2010) 14418-14420. doi: 10.1021/ja107328g
80. [80]
  J. Ni, H. Wang, S.E. Reisman, Tetrahedron 69 (2013) 5622-5633. doi: 10.1016/j.tet.2013.04.003
81. [81]
  M.J. James, J.D. Cuthbertson, P. O'Brien, R.J.K. Taylor, W.P. Unsworth, Angew. Chem. Int. Ed. 54 (2015) 7640-7643. doi: 10.1002/anie.201501812
82. [82]
  Y. Zhao, Y. Tu, M. Cai, J. Zhao, Chin. J. Org. Chem. 42 (2022) 85-99. doi: 10.6023/cjoc202107051
83. [83]
  Y.C. Hu, Y. Zhao, B. Wan, Q.A. Chen, Chem. Soc. Rev. 50 (2021) 2582-2625. doi: 10.1039/d0cs00283f
84. [84]
  T.D. Tan, Z.S. Wang, P.C. Qian, L.W. Ye, Small Methods 5 (2021) 2000673. doi: 10.1002/smtd.202000673
85. [85]
  E.Z. Lin, Y. Xu, K. Ji, L.W. Ye, Chin. Chem. Lett. 32 (2021) 954-962. doi: 10.1016/j.cclet.2020.08.012
86. [86]
  X. Zhou, Z. Liang, X.N. Wang, Chin. J. Org. Chem. 41 (2021) 1288-1318. doi: 10.6023/cjoc202009025
87. [87]
  Y.B. Chen, P.C. Qian, L.W. Ye, Chem. Soc. Rev. 49 (2020) 8897-8909. doi: 10.1039/d0cs00474j
88. [88]
  C.C. Lynch, A. Sripada, C. Wolf, Chem. Soc. Rev. 49 (2020) 8543-8583. doi: 10.1039/d0cs00769b
89. [89]
  F.L. Hong, L.W. Ye, Acc. Chem. Res. 53 (2020) 2003-2019. doi: 10.1021/acs.accounts.0c00417
90. [90]
  J. Luo, G.S. Chen, S.J. Chen, et al., ACS Catal. 10 (2020) 13978-13992. doi: 10.1021/acscatal.0c04180
91. [91]
  B. Zhou, T.D. Tan, X.Q. Zhu, M. Shang, L.W. Ye, ACS Catal. 9 (2019) 6393-6406. doi: 10.1021/acscatal.9b01851
92. [92]
  G. Evano, C. Theunissen, M. Lecomte, Aldrichimica Acta 48 (2015) 59-70.
93. [93]
  X.N. Wang, H.S. Yeom, L.C. Fang, et al., Acc. Chem. Res. 47 (2014) 560-578. doi: 10.1021/ar400193g
94. [94]
  T.D. Tan, X.Q. Zhu, M. Jia, et al., Chin. Chem. Lett. 31 (2020) 1309-1312. doi: 10.1016/j.cclet.2019.10.019
95. [95]
  H.H. Li, S.H. Ye, Y.B. Chen, et al., Chin. J. Chem. 38 (2020) 263-268. doi: 10.1002/cjoc.201900478
96. [96]
  L. Li, X.M. Chen, Z.S. Wang, et al., ACS Catal. 7 (2017) 4004-4010. doi: 10.1021/acscatal.7b01038
97. [97]
  F.L. Hong, C.Y. Shi, P. Hong, et al., Angew. Chem. Int. Ed. 61 (2022) e202115554.
98. [98]
  X.Q. Zhu, P. Hong, Y.X. Zheng, et al., Chem. Sci. 12 (2021) 9466-9474. doi: 10.1039/d1sc02773e
99. [99]
  F.L. Hong, Y.B. Chen, S.H. Ye, et al., J. Am. Chem. Soc. 142 (2020) 7618-7626. doi: 10.1021/jacs.0c01918
100. [100]
  X. Liu, Z.S. Wang, T.Y. Zhai, et al., Angew. Chem. Int. Ed. 59 (2020) 17984-17990. doi: 10.1002/anie.202007206
101. [101]
  F.L. Hong, Z.S. Wang, D.D. Wei, et al., J. Am. Chem. Soc. 141 (2019) 16961-16970. doi: 10.1021/jacs.9b09303
102. [102]
  Z.S. Wang, L.J. Zhu, C.T. Li, et al., Angew. Chem. Int. Ed. 61 (2022) e202201436.
103. [103]
  Y.Q. Zhang, Y.B. Chen, J.R. Liu, et al., Nat. Chem. 13 (2021) 1093-1100. doi: 10.1038/s41557-021-00778-z
104. [104]
  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
105. [105]
  B. Zhou, Y.Q. Zhang, K. Zhang, et al., Nat. Commun. 10 (2019) 3234. doi: 10.1038/s41467-019-11245-2
106. [106]
  Y. Xu, Q. Sun, T.D. Tan, et al., Angew. Chem. Int. Ed. 58 (2019) 16252-16259. doi: 10.1002/anie.201908495
107. [107]
  Y.Q. Zhang, Y.P. Zhang, Y.X. Zheng, Z.Y. Li, L.W. Ye, Cell Rep. Phy. Sci. 2 (2021) 100448. doi: 10.1016/j.xcrp.2021.100448
108. [108]
  H.Z. Bu, H.H. Li, W.F. Luo, et al., Org. Lett. 22 (2020) 648-652. doi: 10.1021/acs.orglett.9b04421
109. [109]
  L. Li, X.Q. Zhu, Y.Q. Zhang, et al., Chem. Sci. 10 (2019) 3123-3129. doi: 10.1039/C9SC00079H
110. [110]
  Y.Q. Zhang, X.Q. Zhu, Y. Xu, et al., Green Chem. 21 (2019) 3023-3028. doi: 10.1039/c9gc01030k
111. [111]
  B.H. Zhu, C.M. Wang, H.Y. Su, L.W. Ye, Chin. J. Chem. 37 (2019) 58-62. doi: 10.1002/cjoc.201800437
112. [112]
  Y. Wang, J. Lin, X. Wang, et al., Chem. Eur. J. 24 (2018) 4026-4032. doi: 10.1002/chem.201705189
113. [113]
  T. Akiyama, K. Mori, Chem. Rev. 115 (2015) 9277-9306. doi: 10.1021/acs.chemrev.5b00041
114. [114]
  D. Parmar, E. Sugiono, S. Raja, M. Rueping, Chem. Rev. 114 (2014) 9047-9153. doi: 10.1021/cr5001496
115. [115]
  T. Akiyama, Chem. Rev. 107 (2007) 5744-5758. doi: 10.1021/cr068374j
116. [116]
  D. Nakashima, H. Yamamoto, J. Am. Chem. Soc. 128 (2006) 9626-9627. doi: 10.1021/ja062508t
1. [1]
  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. Chinese Chemical Letters, 2025, 36(2): 109895-. doi: 10.1016/j.cclet.2024.109895
2. [2]
  Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
3. [3]
  Ruike Hu , Kangmin Wang , Junxiang Liu , Jingxian Zhang , Guoliang Yang , Liqiu Wan , Bijin Li . Extended π-conjugated systems by external ligand-assisted C−H olefination of heterocycles: Facile access to single-molecular white-light-emitting and NIR fluorescence materials. Chinese Chemical Letters, 2025, 36(4): 110113-. doi: 10.1016/j.cclet.2024.110113
4. [4]
  Hongjin Shi , Guoyin Yin , Xi Lu , Yangyang Li . Stereoselective synthesis of 2-deoxy-α-C-glycosides from glycals. Chinese Chemical Letters, 2024, 35(12): 109674-. doi: 10.1016/j.cclet.2024.109674
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]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
7. [7]
  Jiajun Lu , Zhehui Liao , Tongxiang Cao , Shifa Zhu . Synergistic Brønsted/Lewis acid catalyzed atroposelective synthesis of aryl-β-naphthol. Chinese Chemical Letters, 2025, 36(1): 109842-. doi: 10.1016/j.cclet.2024.109842
8. [8]
  Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
9. [9]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
10. [10]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
11. [11]
  Lin Zhang , Chaoran Li , Thongthai Witoon , Xingda An , Le He . Nano-thermometry in photothermal catalysis. Chinese Journal of Structural Chemistry, 2025, 44(4): 100456-100456. doi: 10.1016/j.cjsc.2024.100456
12. [12]
  Junjie Duan , Dan Chen , Long Chen , Shuying Li , Ting Chen , Dong Wang . 2D hexagonal tessellations sustained by Br···Br/H contacts: From regular to semiregular to k-uniform tilings. Chinese Chemical Letters, 2025, 36(3): 110445-. doi: 10.1016/j.cclet.2024.110445
13. [13]
  Yu Mao , Yilin Liu , Xiaochen Wang , Shengyang Ni , Yi Pan , Yi Wang . Acylfluorination of enynes via phosphine and silver catalysis. Chinese Chemical Letters, 2024, 35(8): 109443-. doi: 10.1016/j.cclet.2023.109443
14. [14]
  Jiaqi Jia , Kathiravan Murugesan , Chen Zhu , Huifeng Yue , Shao-Chi Lee , Magnus Rueping . Multiphoton photoredox catalysis enables selective hydrodefluorinations. Chinese Chemical Letters, 2025, 36(2): 109866-. doi: 10.1016/j.cclet.2024.109866
15. [15]
  Ning LI , Siyu DU , Xueyi WANG , Hui YANG , Tao ZHOU , Zhimin GUAN , Peng FEI , Hongfang MA , Shang JIANG . Preparation and efficient catalysis for olefins epoxidation of a polyoxovanadate-based hybrid. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 799-808. doi: 10.11862/CJIC.20230372
16. [16]
  Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896
17. [17]
  Hao-Cong Li , Ming Zhang , Qiyan Lv , Kai Sun , Xiao-Lan Chen , Lingbo Qu , Bing Yu . Homogeneous catalysis and heterogeneous separation: Ionic liquids as recyclable photocatalysts for hydroacylation of olefins. Chinese Chemical Letters, 2025, 36(2): 110579-. doi: 10.1016/j.cclet.2024.110579
18. [18]
  Jing Guo , Zhi-Guo Lu , Rui-Chen Zhao , Bao-Ku Li , Xin Zhang . Nucleic acid therapy for metabolic-related diseases. Chinese Chemical Letters, 2025, 36(3): 109875-. doi: 10.1016/j.cclet.2024.109875
19. [19]
  Yuan Teng , Zichun Zhou , Jinghua Chen , Siying Huang , Hongyan Chen , Daibin Kuang . Dual atom-bridge effect promoting interfacial charge transfer in 2D/2D Cs₃Bi₂Br₉/BiOBr epitaxial heterojunction for efficient photocatalysis. Chinese Chemical Letters, 2025, 36(2): 110430-. doi: 10.1016/j.cclet.2024.110430
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(441)
HTML views(77)

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