Citation: Xuling Pan, Wei Cai, You Huang. Recent advances in phosphine-mediated sequential annulations[J]. Chinese Chemical Letters, ;2025, 36(5): 110628. doi: 10.1016/j.cclet.2024.110628 shu

Recent advances in phosphine-mediated sequential annulations

State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China

hyou@nankai.edu.cn

Received Date: 30 June 2024
Revised Date: 27 October 2024
Accepted Date: 7 November 2024
Available Online: 9 November 2024

Figures(53)

Polycyclic compounds are widely found in natural products and drug molecules with important biological activities, which attracted the attention of many chemists. Phosphine-catalyzed nucleophilic addition is one of the most powerful tools for the construction of various cyclic compounds with the advantages of atom economy, mild reaction conditions and simplicity of operation. Allenolates, Morita−Baylis−Hillman (MBH) alcohols and their derivatives (MBHADs), electron-deficient olefins and alkynes are very efficient substrates in phosphine mediated annulations, which formed many phosphonium species such as β-phosphonium enolates, β-phosphonium dienolates and vinyl phosphonium ylides as intermediates. This review describes the reactivities of these phosphonium zwitterions and summarizes the synthesis of polycycle compounds through phosphine-mediated intramolecular and intermolecular sequential annulations. Thus, a systematic summary of the research process based on the phosphine-mediated sequential annulations of allenolates, MBH alcohols and MBHADs, electron-deficient olefins and alkynes are presented in Chapters 2–6, respectively.
- Phosphine catalysis,
- Sequential annulations,
- Polycyclic compounds,
- Synthetic methods
1. [1]
  D. Crich, A. Banerjee, Acc. Chem. Res. 40 (2007) 151–161. doi: 10.1021/ar050175j
2. [2]
  D. Zhang, H. Song, Y. Qin, Acc. Chem. Res. 44 (2011) 447–457. doi: 10.1021/ar200004w
3. [3]
  W. Zi, Z. Zuo, D. Ma, Acc. Chem. Res. 48 (2015) 702–711. doi: 10.1021/ar5004303
4. [4]
  R. Ardkhean, D.F.J. Caputo, S. Morrow, et al., Chem. Soc. Rev. 45 (2016) 1557–1569. doi: 10.1039/C5CS00105F
5. [5]
  H. Takikawa, A. Nishii, T. Sakai, K. Suzuki, Chem. Soc. Rev. 47 (2018) 8030–8056. doi: 10.1039/c8cs00350e
6. [6]
  M. Lin, F. Li, L. Jiao, et al., J. Am. Chem. Soc. 133 (2011) 1690–1693. doi: 10.1021/ja110039h
7. [7]
  L. Jiao, M. Lin, Z.X. Yu, J. Am. Chem. Soc. 133 (2011) 447–461. doi: 10.1021/ja107396t
8. [8]
  M. Lin, G.Y. Kang, Y.A. Guo, et al., J. Am. Chem. Soc. (134) 2012 398–405. doi: 10.1021/ja2082119
9. [9]
  J. Wang, Y. Phang, Y.J. Yu, et al., Angew. Chem. Int. Ed. 63 (2024) e202405863. doi: 10.1002/anie.202405863
10. [10]
  P. Shiri, A. Roosta, W. Dehaen, et al., Molecules 27 (2022) 4942–4983. doi: 10.3390/molecules27154942
11. [11]
  A. Baccalini, G. Faita, G. Zanoni, et al., Chem. Eur. J. 26 (2020) 9749–9783. doi: 10.1002/chem.202001832
12. [12]
  X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 34 (2001) 535–544. doi: 10.1021/ar000253x
13. [13]
  L.W. Ye, J. Zhou, Y. Tang, Chem. Soc. Rev. 37 (2008) 1140–1152. doi: 10.1039/b717758e
14. [14]
  D. Basavaiah, B.S. Reddy, S.S. Badsara, Chem. Rev. 110 (2010) 5447–5674. doi: 10.1021/cr900291g
15. [15]
  F. Lopez, J.L. Mascarenas, Chem. Soc. Rev. 43 (2014) 2904–2915. doi: 10.1039/C4CS00024B
16. [16]
  A. Marinetti, A. Voituriez, M. Gicquel, Synlett (2014) 142–166.
17. [17]
  D. En, G.F. Zou, Y. Guo, et al., J. Org. Chem. 79 (2014) 4456–4462. doi: 10.1021/jo500418s
18. [18]
  J. Zhang, C. Cheng, D. Wang et al., J. Org. Chem. 82 (2017) 10121–10128. doi: 10.1021/acs.joc.7b01582
19. [19]
  G. Wittig, U. Schollkopf, Chem. Ber. 87 (1954) 1318–1330. doi: 10.1002/cber.19540870919
20. [20]
  H. Staudinger, J.H. Meyer, Chim. Acta 2 (1919) 635–646. doi: 10.1002/hlca.19190020164
21. [21]
  R. Appel, Angew. Chem. Int. Ed. 14 (1975) 801–811. doi: 10.1002/anie.197508011
22. [22]
  O. Mitsunobu, M. Yamada, Bull. Chem. Soc. Jpn. 40 (1967) 2380. doi: 10.1246/bcsj.40.2380
23. [23]
  S.H. Newman-Stonebraker, R.S. Sleight, E.B. Julia, et al., Science 374 (2021) 301–308. doi: 10.1126/science.abj4213
24. [24]
  C.C.C. Johansson Seechurn, M.O. Kitching, T.J. Colacot, V. Snieckus, Angew. Chem. Int. Ed. 51 (2012) 5062–5085. doi: 10.1002/anie.201107017
25. [25]
  C. Zhang, X. Lu, J. Org. Chem. 60 (1995) 2906–2908. doi: 10.1021/jo00114a048
26. [26]
  X.F. Zhu, J. Lan, O. Kwon, J. Am. Chem. Soc. 125 (2003) 4716–4717. doi: 10.1021/ja0344009
27. [27]
  Q. Zhang, L. Yang, X. Tong, J. Am. Chem. Soc. 132 (2010) 2550–2551. doi: 10.1021/ja100432m
28. [28]
  E. Li, Y. Huang, L. Liang, et al., Org. Lett. 15 (2013) 3138–3141. doi: 10.1021/ol401249e
29. [29]
  S.V. Mudur, D.C. Swenson, B.G. Swenson, et al., Org. Lett. 8 (2006) 3191–3194. doi: 10.1021/ol060916w
30. [30]
  R.A. Jones, M.J. Krische, Org. Lett. 11 (2009) 1849–1851. doi: 10.1021/ol900360h
31. [31]
  M. Sampath, P.Y.B. Lee, T.P. Loh, Chem. Sci. 2 (2011) 1988–1991. doi: 10.1039/c1sc00311a
32. [32]
  R.A. Villa, Q. Xu, O. Kwon, Org. Lett. 14 (2012) 4634–4637. doi: 10.1021/ol302077n
33. [33]
  X. Han, F. Zhong, Y. Wang, et al., Angew. Chem. Int. Ed. 51 (2012) 767–770. doi: 10.1002/anie.201106672
34. [34]
  I.P. Andrews, O. Kwon, Chem. Sci. 3 (2012) 2510–2514. doi: 10.1039/c2sc20468a
35. [35]
  T. Wang, W. Yao, F. Zhong, et al., Angew. Chem. Int. Ed. 53 (2014) 2964–2968. doi: 10.1002/anie.201307757
36. [36]
  X. Han, W. Yao, T. Wang, et al., Angew. Chem. Int. Ed. 53 (2014) 5643–5647. doi: 10.1002/anie.201311214
37. [37]
  L. Cai, K. Zhang, O. Kwon, J. Am. Chem. Soc. 138 (2016) 3298–3301. doi: 10.1021/jacs.6b00567
38. [38]
  J. Li, W. Zhang, F. Zhang, et al., J. Am. Chem. Soc. 139 (2017) 14893–14896. doi: 10.1021/jacs.7b09186
39. [39]
  Y. Chen, W. Zhang, L. Ren, et al., Angew. Chem. Int. Ed. 57 (2018) 952–956. doi: 10.1002/anie.201711482
40. [40]
  W.L. Chan, X. Tang, F. Zhang, et al., Angew. Chem. Int. Ed. 58 (2019) 6260–6264. doi: 10.1002/anie.201900758
41. [41]
  C.X.A. Tan, Rui. Li, L. Dai, et al., Angew. Chem. Int. Ed. 61 (2022) e202209494. doi: 10.1002/anie.202209494
42. [42]
  Z. Xu, X. Lu, J. Org. Chem. 63 (1998) 5031–5041. doi: 10.1021/jo9723063
43. [43]
  X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 34 (2001) 535–544. doi: 10.1021/ar000253x
44. [44]
  J.L. Methot, W.R. Roush, Adv. Synth. Catal. 346 (2004) 1035–1050. doi: 10.1002/adsc.200404087
45. [45]
  L.W. Ye, J. Zhou, Y. Tang, Chem. Soc. Rev. 37 (2008) 1140–1152. doi: 10.1039/b717758e
46. [46]
  Y. Fan, O. Kwon, Chem. Commun. 49 (2013) 11588–11619. doi: 10.1039/c3cc47368f
47. [47]
  Z. Wang, X. Xu, O. Kwon, Chem. Soc. Rev. 43 (2014) 2927–2940. doi: 10.1039/C4CS00054D
48. [48]
  Y. Xiao, Z. Sun, H. Guo, O. Kwon, Beilstein J. Org. Chem. 10 (2014) 2089–2121. doi: 10.3762/bjoc.10.218
49. [49]
  Y. Xiao, H. Guo, O. Kwon, Aldrichimica Acta. 49 (2016) 3–13.
50. [50]
  T. Wang, X. Han, F. Zhong, et al., Acc. Chem. Res. 49 (2016) 1369–1378. doi: 10.1021/acs.accounts.6b00163
51. [51]
  W. Li, J. Zhang, Chem. Soc. Rev. 45 (2016) 1657–1677. doi: 10.1039/C5CS00469A
52. [52]
  Y. Wei, M. Shi, Org. Chem. Front. 4 (2017) 1876–1890. doi: 10.1039/C7QO00285H
53. [53]
  H. Ni, W.L. Chan, Y. Lu, Chem. Rev. 118 (2018) 9344–9411. doi: 10.1021/acs.chemrev.8b00261
54. [54]
  H. Guo, Y.C. Fan, Z. Sun, et al., Chem. Rev. 118 (2018) 10049–10293. doi: 10.1021/acs.chemrev.8b00081
55. [55]
  E. Li, Y. Huang, Chem. Commun. 56 (2020) 680–694. doi: 10.1039/c9cc08241g
56. [56]
  Y. Huang, J. Liao, W. Wang, et al., Chem. Commun. 56 (2020) 15235–15281. doi: 10.1039/d0cc05699e
57. [57]
  Y. Wei, M. Shi, Chin. J. Chem. 38 (2020) 1395–1421. doi: 10.1002/cjoc.202000160
58. [58]
  C. Xie, A.J. Smaligo, X. Song, O. Kwon, ACS Cent. Sci. 7 (2021) 536–558. doi: 10.1021/acscentsci.0c01493
59. [59]
  F. An, H. Jangra, Y. Wei, et al., Chem. Commun. 58 (2022) 3358–3361. doi: 10.1039/d1cc06786a
60. [60]
  X. Li, W. Cai, Y. Huang, Adv. Synth. Catal. 364 (2022) 1879–1883. doi: 10.1002/adsc.202200071
61. [61]
  J. Szeto, V. Sriramurthy, O. Kwon, Org. Lett. 13 (2011) 5420–5423. doi: 10.1021/ol201730q
62. [62]
  M. Song, J. Zhao, E.Q. Li, Chin. Chem. Lett. 33 (2022) 2372–2382. doi: 10.1016/j.cclet.2021.11.044
63. [63]
  C.E. Henry, O. Kwon, Org. Lett. 9 (2007) 3069–3072. doi: 10.1021/ol071181d
64. [64]
  S.Y. Lee, Y. Fujiwara, A. Nishiguchi, et al., J. Am. Chem. Soc. 137 (2015) 4587–4591. doi: 10.1021/jacs.5b01985
65. [65]
  W. Yao, Z. Yu, S. Wen, et al., Chem. Sci. 8 (2017) 5196–5200. doi: 10.1039/C7SC00952F
66. [66]
  L.J. Yang, S. Wang, J. Nie, et al., Org. Lett. 15 (2013) 5214–5217. doi: 10.1021/ol402364t
67. [67]
  S. Ma, A. Yu, L. Zhang, et al., J. Org. Chem. 83 (2018) 5410–5419. doi: 10.1021/acs.joc.8b00145
68. [68]
  M. Kondo, H.D.P. Wathsala, M. Sako, et al., Chem. Commun. 56 (2020) 1259–1262. doi: 10.1039/c9cc08526b
69. [69]
  N. Wang, Y. Lang, J. Wang, et al., Org. Lett. 24 (2022) 3712–3716. doi: 10.1021/acs.orglett.2c01352
70. [70]
  Y.H. Wang, S.J. Kalita, W.L. Li, et al., Adv. Synth. Catal. 364 (2022) 3690–3696. doi: 10.1002/adsc.202200739
71. [71]
  Y. Gu, P. Hu, C. Ni, et al., J. Am. Chem. Soc. 137 (2015) 6400–6406. doi: 10.1021/jacs.5b03273
72. [72]
  J.J. Xing, Y.N. Gao, M. Shi, Adv. Synth. Catal. 360 (2018) 2552–2559. doi: 10.1002/adsc.201800319
73. [73]
  Z. Dai, J. Zhu, J. Wang, et al., Adv. Synth. Catal. 362 (2020) 545–551. doi: 10.1002/adsc.201901132
74. [74]
  C.G. Neochoritis, C.A. Tsoleridis, J. Stephanidou-Stephanatou, et al., J. Med. Chem. 53 (2010) 8409–8420. doi: 10.1021/jm100739n
75. [75]
  J.F. Liegeois, M. Deville, S. Dilly, et al., J. Med. Chem. 55 (2012) 1572–1582. doi: 10.1021/jm2013419
76. [76]
  H. Zhao, X. Meng, Y. Huang, Chem. Commun. 49 (2013) 10513–10515. doi: 10.1039/c3cc46379f
77. [77]
  J. Zheng, Y. Huang, Z. Li, Org. Lett. 15 (2013) 5758–5761. doi: 10.1021/ol402799w
78. [78]
  E. Li, Y. Huang, Chem. Commun. 50 (2014) 948–950. doi: 10.1039/C3CC47716A
79. [79]
  E. Li, Y. Huang, Chem. Eur. J. 20 (2014) 3520–3527. doi: 10.1002/chem.201304003
80. [80]
  E. Li, P. Jia, L. Liang, et al., ACS Catal. 4 (2014) 600–603. doi: 10.1021/cs401161q
81. [81]
  E. Li, H. Jin, P. Jia, et al., Angew. Chem. Int. Ed. 55 (2016) 11591–11594. doi: 10.1002/anie.201605189
82. [82]
  M. Wu, Z. Han, K. Li, et al., J. Am. Chem. Soc. 141 (2019) 16362–16373. doi: 10.1021/jacs.9b07418
83. [83]
  J. Feng, Y. Huang, Chem. Commun. 55 (2019) 14011–14014. doi: 10.1039/c9cc07346a
84. [84]
  J. Feng, Y. Chen, W. Qin, et al., Org. Lett. 22 (2020) 433–437. doi: 10.1021/acs.orglett.9b04176
85. [85]
  X. Li, Y. Huang, Chem. Commun. 57 (2021) 9934–9937. doi: 10.1039/d1cc04199a
86. [86]
  M. Ma, J. Feng, W. Cai, et al., Org. Lett. 26 (2024) 4037–4042. doi: 10.1021/acs.orglett.4c00656
87. [87]
  N. Li, P. Jia, Y. Huang, Chem. Commun. 55 (2019) 10976–10979. doi: 10.1039/c9cc05832j
88. [88]
  N. Li, Y. Huang, Org. Lett. 22 (2020) 9392–9397. doi: 10.1021/acs.orglett.0c03725
89. [89]
  Z. Dai, J. Zhu, W. Su, et al., Org. Lett. 22 (2020) 7008–7012. doi: 10.1021/acs.orglett.0c02558
90. [90]
  Z. Duan, M. Liu, B. Zheng, et al., Org. Lett. 25 (2023) 3298–3302. doi: 10.1021/acs.orglett.3c01066
91. [91]
  Y. Du, X. Lu, C. Zhang, Angew. Chem. Int. Ed. 42 (2003) 1035–1037. doi: 10.1002/anie.200390266
92. [92]
  L.W. Ye, X.L. Sun, Q.G. Wang, et al., Angew. Chem. Int. Ed. 46 (2007) 5951–5954. doi: 10.1002/anie.200701460
93. [93]
  L.W. Ye, X. Han, X.L. Sun, et al., Tetrahedron 64 (2008) 1487–1493. doi: 10.1016/j.tet.2007.11.052
94. [94]
  X. Han, L.W. Ye, X.L. Sun, et al., J. Org. Chem. 74 (2009) 3394–3397. doi: 10.1021/jo9001917
95. [95]
  Q. Wang, S.F. Zhu, L.W. Ye, et al., Adv. Synth. Catal. 352 (2010) 1914–1919. doi: 10.1002/adsc.201000129
96. [96]
  W.A. Donaldson, Tetrahedron 57 (2001) 8589–8627. doi: 10.1016/S0040-4020(01)00777-3
97. [97]
  R. Sarpong, J.T. Su, B.M. Stoltz, J. Am. Chem. Soc. 125 (2003) 13624–13625. doi: 10.1021/ja037587c
98. [98]
  E.L. Fisher, S.M. Wilkerson-Hill, R. Sarpong, J. Am. Chem. Soc. 134 (2012) 9946–9949. doi: 10.1021/ja3045647
99. [99]
  M.C.P. Yeh, C.J. Liang, C.W. Fan, et al., J. Org. Chem. 77 (2012) 9707–9717. doi: 10.1021/jo301764g
100. [100]
  J. Zheng, Y. Huang, Z. Li, Chem. Commun. 50 (2014) 5710–5713. doi: 10.1039/c4cc01097c
101. [101]
  Y. Du, J. Feng, X. Lu, Org. Lett. 7 (2005) 1987–1989. doi: 10.1021/ol050443d
102. [102]
  J. Feng, X. Lu, A. Kong, et al., Tetrahedron 63 (2007) 6035–6041. doi: 10.1016/j.tet.2007.02.115
103. [103]
  S. Zheng, X. Lu, Org. Lett. 10 (2008) 4481–4484. doi: 10.1021/ol801661y
104. [104]
  S. Zheng, X. Lu, Org. Lett. 11 (2009) 3978–3981. doi: 10.1021/ol901618h
105. [105]
  S. Zheng, X. Lu, Tetrahedron Lett. 50 (2009) 4532–4535. doi: 10.1016/j.tetlet.2009.05.085
106. [106]
  B. Tan, N.R. Candeias, C.F. Barbas, J. Am. Chem. Soc. 133 (2011) 4672–4675. doi: 10.1021/ja110147w
107. [107]
  R. Zhou, J. Wang, H. Song, et al., Org. Lett. 13 (2011) 580–583. doi: 10.1021/ol102738b
108. [108]
  F. Zhong, X. Han, Y. Wang, et al., Angew. Chem. Int. Ed. 50 (2011) 7837–7841. doi: 10.1002/anie.201102094
109. [109]
  P. Xie, Y. Huang, R. Chen, Chem. Eur. J. 18 (2012) 7362–7366. doi: 10.1002/chem.201200305
110. [110]
  F. Zhong, G.Y. Chen, X. Han, et al., Org. Lett. 14 (2012) 3764–3767. doi: 10.1021/ol301647g
111. [111]
  R. Zhou, J. Wang, C. Duan, et al., Org. Lett. 14 (2012) 6134–6137. doi: 10.1021/ol302696e
112. [112]
  H. Xiao, H.Y. Duan, J. Ye, et al., Org. Lett. 16 (2014) 5462–5465. doi: 10.1021/ol502709w
113. [113]
  L. Zhang, H. Liu, G. Qiao, et al., J. Am. Chem. Soc. 137 (2015) 4316–4319. doi: 10.1021/jacs.5b01138
114. [114]
  Z. Chen, J. Zhang, Chem. Asian J. 5 (2010) 1542–1545. doi: 10.1002/asia.201000193
115. [115]
  P. Xie, Y. Huang, R. Chen, Org. Lett. 12 (2010) 3768–3771. doi: 10.1021/ol101611v
116. [116]
  J. Tian, R. Zhou, H. Sun, et al., J. Org. Chem. 76 (2011) 2374–2378. doi: 10.1021/jo200164v
117. [117]
  X.N. Zhang, H.P. Deng, L. Huang, et al., Chem. Commun. 48 (2012) 8664–8666. doi: 10.1039/c2cc34619b
118. [118]
  P. Xie, J. Yang, J. Zheng, et al., Eur. J. Org. Chem. 2014 (2014) 1189–1194. doi: 10.1002/ejoc.201301872
119. [119]
  P. Xie, E. Li, J. Zheng, et al., Adv. Synth. Catal. 355 (2013) 161–169. doi: 10.1002/adsc.201200675
120. [120]
  Q. Zhang, Y. Zhu, H. Jin, et al., Chem. Commun. 53 (2017) 3974–3977. doi: 10.1039/C6CC10155K
121. [121]
  J. Jia, A. Yu, S. Ma, et al., Org. Lett. 19 (2017) 6084–6087. doi: 10.1021/acs.orglett.7b02916
122. [122]
  S. Ma, A. Yu, S. Zhang, et al., J. Org. Chem. 85 (2020) 7884–7895. doi: 10.1021/acs.joc.0c00566
123. [123]
  H. Li, W. Shi, C. Wang, et al., Org. Lett. 23 (2021) 5571–5575. doi: 10.1021/acs.orglett.1c01975
124. [124]
  J. Lin, Y. Zhu, W. Cai, et al., Org. Lett. 24 (2022) 1593–1597. doi: 10.1021/acs.orglett.1c04388
125. [125]
  Y. Zhu, H. Zhao, Q. Li, et al., Adv. Synth. Catal. 366 (2024) 1–6.
126. [126]
  L. Zhou, C. Yuan, Y. Zeng et al., Org. Lett. 21 (2019) 4882–4886. doi: 10.1021/acs.orglett.9b01783
127. [127]
  L. Horner, W. Jurgeleit, K. Klupfel, Ann. Liebigs, Chem 591 (1955) 108–117. doi: 10.1002/jlac.19555910107
128. [128]
  M.M. Rauhut, H. Currier, U.S. Patent 3074999, 1963.
129. [129]
  K. Morita, Z. Suzuki, H. Hirose, Bull. Chem. Soc. Jpn. 41 (1968) 2815–2816. doi: 10.1246/bcsj.41.2815
130. [130]
  M. Couturier, F. Me´nard, J.A. Ragan, Org. Lett. 6 (2004) 1857–1860. doi: 10.1021/ol049392v
131. [131]
  R.K. Thalji, W.R. Roush, J. Am. Chem. Soc. 127 (2005) 16778–16779. doi: 10.1021/ja054085l
132. [132]
  Z. Jin, R. Yang, Y. Du, et al., Org. Lett. 14 (2012) 3226–3229. doi: 10.1021/ol3013588
133. [133]
  J.M. Yang, X.Y. Tang, Y. Wei, et al., Adv. Synth. Catal. 355 (2013) 3545–3552. doi: 10.1002/adsc.201300875
134. [134]
  J.P. Mauryu, S.S.V. Ramasastry, Org. Lett. 26 (2024) 2282–2286. doi: 10.1021/acs.orglett.4c00481
135. [135]
  N.T. McDougal, S.E. Schaus, Angew. Chem. Int. Ed. 45 (2006) 3117–3119. doi: 10.1002/anie.200600126
136. [136]
  J. Ma, P. Xie, C. Hu, et al., Chem. Eur. J. 17 (2011) 7418–7422. doi: 10.1002/chem.201100881
137. [137]
  E. Winterfeldt, H.J. Dillinger, Chem. Ber. 99 (1966) 1558–1568. doi: 10.1002/cber.19660990520
138. [138]
  K. Nozaki, N. Sato, K.J. Ikeda, J. Org. Chem. 61 (1996) 4516–4519. doi: 10.1021/jo951828k
139. [139]
  J.C. Wang, S.S. Ng, M.J. Krische, J. Am. Chem. Soc. 125 (2003) 3682–3683. doi: 10.1021/ja030022w
140. [140]
  J.C. Wang, M.J. Krische, Angew. Chem. Int. Ed. 42 (2003) 5855–5857. doi: 10.1002/anie.200352218
141. [141]
  J.E. Wilson, J. Sun, G.C. Fu, Angew. Chem. Int. Ed. 49 (2010) 161–163. doi: 10.1002/anie.200905125
142. [142]
  C.T. Mbofana, S.J. Miller, ACS Catal. 4 (2014) 3671–3674. doi: 10.1021/cs501117h
143. [143]
  C.Z. Zhu, Y.L. Sun, Y. Wei, et al., Adv. Synth. Catal. 359 (2017) 1263–1270. doi: 10.1002/adsc.201700031
144. [144]
  L. Liang, X. Dong, Y. Huang, Chem. Eur. J. 23 (2017) 7882–7886. doi: 10.1002/chem.201701026
145. [145]
  Y.S. Chen, Y. Zheng, Z.J. Chen, et al., Org. Biomol. Chem. 19 (2021) 7074–7080. doi: 10.1039/d1ob01143j
146. [146]
  Y.S. Chen, Y. Zheng, K. Tang, Org. Biomol. Chem. 20 (2022) 4415–4420. doi: 10.1039/d2ob00603k
147. [147]
  S.S. Vagh, B.J. Hou, A. Edukondalu, et al., Org. Lett. 23 (2021) 842–846. doi: 10.1021/acs.orglett.0c04082
148. [148]
  S.S. Vagh, B.J. Hou, A. Edukondalu, et al., Adv. Synth. Catal. 363 (2021) 5429–5435. doi: 10.1002/adsc.202100899
149. [149]
  K. Liu, G. Wang, Z.W. Zhang, et al., Org. Lett. 24 (2022) 6489–6493. doi: 10.1021/acs.orglett.2c02201
150. [150]
  J.B. Zhu, H. Chen, S. Liao, et al., Org. Chem. Front. 1 (2014) 1035–1039. doi: 10.1039/C4QO00232F
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沈阳化工大学材料科学与工程学院沈阳 110142