Citation: Yunhao Guan, Xia Peng, Rong Fan, Xiaoying Feng, Hongguang Du, Jiajing Tan. Precise synthesis of ortho-deuterated aromatic derivatives: An arylthianthrenium salt-based platform approach[J]. Chinese Chemical Letters, ;2026, 37(1): 111132. doi: 10.1016/j.cclet.2025.111132 shu

Precise synthesis of ortho-deuterated aromatic derivatives: An arylthianthrenium salt-based platform approach

Department of Organic Chemistry, Beijing University of Chemical Technology, Beijing 100029, China

dhg@mail.buct.edu.cn

jiajing.tan@foxmail.com

Received Date: 17 December 2024
Revised Date: 11 March 2025
Accepted Date: 20 March 2025
Available Online: 21 March 2025

Figures(4)

The deuterium labeling has garnered significant interest in drug discovery due to its critical role on improving pharmacokinetic and metabolic properties. However, despite its pharmaceutical value, the general and rapid syntheses of aromatic scaffolds that contains deuterium remain an important yet elusive task. State-of-the-art approaches mainly relied on the transition metal-catalyzed C–H deuteration via the assistance of directing groups (DGs), which often suffered from over-deuteration and lengthy step counts required for installation and/or removal of DG. Herein, we report a generalizable synthetic linchpin strategy for the facile preparation of the ortho-deuterated aromatic core. Through capture of aryne-derived 1,3-zwitterion with heavy water, we synthesized an array of ortho-deuterated aryl sulfonium salts. These novel linchpins not only participated the transition metal catalyzed cross-coupling reaction as nucleophiles, but also served as aryl radical reservoirs under photochemical or electrochemical conditions, enabling facile and precise access to structurally diverse deuterated aromatics. Moreover, we have disclosed a novel EDA complex enabled direct arylation of phosphines under visible-light irradiation, further expanding the utility of our platform approach.
- Deuterium labeling,
- Thianthrenium salts,
- Precise synthesis,
- Linchpin strategy,
- Aryne chemistry,
- Organosulfur chemistry
1. [1]
  R. Zhou, L. Ma, X. Yang, J. Cao, Org. Chem. Front. 8 (2021) 426–444. doi: 10.1039/d0qo01299h
2. [2]
  Y. Guo, Z. Zhuang, Y. Liu, et al., Coord. Chem. Rev. 463 (2022) 214525. doi: 10.1016/j.ccr.2022.214525
3. [3]
  N. Li, Y. Li, X. Wu, C. Zhu, J. Xie, Chem. Soc. Rev. 51 (2022) 6291–6306. doi: 10.1039/d1cs00907a
4. [4]
  G. Prakash, N. Paul, G.A. Oliver, D.B. Werz, D. Maiti, Chem. Soc. Rev. 51 (2022) 3123–3163. doi: 10.1039/d0cs01496f
5. [5]
  H.M. Chandra Mouli, A. Vinod, S. Kumari, et al., Bioorg. Chem. 135 (2023) 106490. doi: 10.1016/j.bioorg.2023.106490
6. [6]
  J. Atzrodt, V. Derdau, W.J. Kerr, M. Reid, Angew. Chem. Int. Ed. 57 (2018) 1758–1784. doi: 10.1002/anie.201704146
7. [7]
  M.G. Horning, J.P. Thenot, O. Bouwsma, J. Nowlin, K. Lertratanangkoon, Adv. Pharmacol. Ther, Proc. Int. Congr. Pharmacol. 7 (1978) 245–256.
8. [8]
  A.C. Flick, H.X. Ding, C.A. Leverett, et al., J. Med. Chem. 60 (2017) 6480–6515. doi: 10.1021/acs.jmedchem.7b00010
9. [9]
  T.G. Gant, J. Med. Chem. 57 (2014) 3595–3611. doi: 10.1021/jm4007998
10. [10]
  T. Pirali, M. Serafini, S. Cargnin, A.A. Genazzani, J. Med. Chem. 62 (2019) 5276–5297. doi: 10.1021/acs.jmedchem.8b01808
11. [11]
  J.C.M. Low, A.J. Wright, F. Hesse, J. Cao, K.M. Brindle, Prog. Nucl. Magn. Reson. Spectrosc. 134–135 (2023) 39–51. doi: 10.1093/oso/9780197543733.003.0003
12. [12]
  S. Kopf, F. Bourriquen, W. Li, et al., Chem. Rev. 122 (2022) 6634–6718. doi: 10.1021/acs.chemrev.1c00795
13. [13]
  A. Katsnelson, Nat. Med. 19 (2013) 656. doi: 10.1038/nm0613-656
14. [14]
  R.M.C. Di Martino, B.D. Maxwell, T. Pirali, Nat. Rev. Drug. Discov. 22 (2023) 562–584. doi: 10.1038/s41573-023-00703-8
15. [15]
  C. Schmidt, Nat. Biotechnol. 35 (2017) 493–494. doi: 10.1038/nbt0617-493
16. [16]
  L. Liu, Z. Deng, K. Xu, et al., Org. Lett. 23 (2021) 5299–5304. doi: 10.1021/acs.orglett.1c01448
17. [17]
  J. Atzrodt, V. Derdau, T. Fey, J. Zimmermann, Angew. Chem. Int. Ed. 46 (2007) 7744–7765. doi: 10.1002/anie.200700039
18. [18]
  J. Atzrodt, V. Derdau, W.J. Kerr, M. Reid, Angew. Chem. Int. Ed. 57 (2018) 3022–3047. doi: 10.1002/anie.201708903
19. [19]
  Q. Sun, J.F. Soulé, Chem. Soc. Rev. 50 (2021) 10806–10835. doi: 10.1039/d1cs00544h
20. [20]
  P.L. Norcott, Chem. Commun. 58 (2022) 2944–2953. doi: 10.1039/d2cc00344a
21. [21]
  M. Gómez-Gallego, M.A. Sierra, Inorg. Chem. Front. 8 (2021) 3934–3950. doi: 10.1039/d1qi00505g
22. [22]
  H. Li, M. Peng, L. Wang, et al., Org. Lett. 26 (2024) 719–723. doi: 10.1021/acs.orglett.3c04155
23. [23]
  Y. Ding, S. Luo, C. Weng, J. An, J. Org. Chem. 84 (2019) 15098–15105. doi: 10.1021/acs.joc.9b02056
24. [24]
  X. Li, J. Zhou, W. Deng, et al., Chem. Sci. 15 (2024) 11418–11427. doi: 10.1039/d4sc03049d
25. [25]
  S. Ning, C. Wu, L. Zheng, et al., Green Chem. 25 (2023) 9993–9997. doi: 10.1039/d3gc02345a
26. [26]
  W. Li, R. Qu, W. Liu, et al., Chem. Sci. 12 (2021) 14033–14038. doi: 10.1039/d1sc04259a
27. [27]
  A. Tortajada, E. Hevia, Catal. Sci. Technol. 13 (2023) 4919–4925. doi: 10.1039/d3cy00825h
28. [28]
  W.J. Kerr, G.J. Knox, M. Reid, T. Tuttle, Chem. Sci. 12 (2021) 6747–6755. doi: 10.1039/d1sc01509e
29. [29]
  N. Li, Y. Ning, X. Wu, et al., Chem. Sci. 12 (2021) 5505–5510. doi: 10.1039/d1sc00528f
30. [30]
  L. Guo, C. Xu, D.C. Wu, et al., Chem. Commun. 55 (2019) 8567–8570. doi: 10.1039/c9cc03988k
31. [31]
  H. Xu, M. Liu, L.J. Li, et al., Org. Lett. 21 (2019) 4887–4891. doi: 10.1021/acs.orglett.9b01784
32. [32]
  Y. Fan, W. Ou, M. Chen, et al., Org. Lett. 25 (2023) 432–437. doi: 10.1021/acs.orglett.2c04154
33. [33]
  B.Q. He, X. Wu, Org. Lett. 25 (2023) 6571–6576. doi: 10.1021/acs.orglett.3c02432
34. [34]
  C.H. Hu, Y. Li, J. Org. Chem. 88 (2023) 6401–6406. doi: 10.1021/acs.joc.2c02299
35. [35]
  J.L. Lu, J.T. Deng, M. Lang, J.B. Peng, Org. Chem. Front. 11 (2024) 5473–5478. doi: 10.1039/d4qo00956h
36. [36]
  S. Liu, H. Liao, B. Chen, et al., Green Chem. 26 (2024) 10456–10462. doi: 10.1039/d4gc01134a
37. [37]
  M. Lecomte, M. Lahboubi, P. Thilmany, A.E. Bouzakhi, G. Evano, Chem. Sci. 12 (2021) 11157–11165. doi: 10.1039/d1sc02622d
38. [38]
  J. Dong, X. Wang, Z. Wang, et al., Chem. Sci. 11 (2020) 1026–1031. doi: 10.1039/c9sc05132e
39. [39]
  E. Martinelli, M. Spiller, R. Weck, et al., Chem. Eur. J. 30 (2024) e202402038. doi: 10.1002/chem.202402038
40. [40]
  M. Itoga, M. Yamanishi, T. Udagawa, et al., Chem. Sci. 13 (2022) 8744–8751. doi: 10.1039/d2sc01805e
41. [41]
  M. Valero, T. Kruissink, J. Blass, et al., Angew. Chem. Int. Ed. 59 (2020) 5626–5631. doi: 10.1002/anie.201914220
42. [42]
  W. Liu, L. Cao, Z. Zhang, et al., Org. Lett. 22 (2020) 2210–2214. doi: 10.1021/acs.orglett.0c00402
43. [43]
  W.J. Kerr, M. Reid, T. Tuttle, ACS Catal. 5 (2015) 402–410. doi: 10.1021/cs5015755
44. [44]
  C.M. Stork, R. Weck, M. Valero, et al., Angew. Chem. Int. Ed. 135 (2023) e202301512. doi: 10.1002/ange.202301512
45. [45]
  M.H. Emmert, J.B. Gary, J.M. Villalobos, M.S. Sanford, Angew. Chem. Int. Ed. 49 (2010) 5884–5886. doi: 10.1002/anie.201002351
46. [46]
  M. Yamamoto, Y. Yokota, K. Oshima, S. Matsubara, Chem. Commun. (2004) 1714–1715.
47. [47]
  A.J. Hickman, M.A. Cismesia, M.S. Sanford, Organometallics 31 (2012) 1761–1766. doi: 10.1021/om201105b
48. [48]
  Y. Sawama, T. Yamada, Y. Yabe, et al., Adv. Synth. Catal. 355 (2013) 1529–1534. doi: 10.1002/adsc.201201102
49. [49]
  C. Zheng, J. Xue, Z.J. Jiang, et al., Chem. Commun. 60 (2024) 10338–10341. doi: 10.1039/D4CC03089C
50. [50]
  J. Li, Q. Lin, O. Dungan, et al., J. Am. Chem. Soc. 146 (2024) 31497–31506. doi: 10.1021/jacs.4c08176
51. [51]
  C. Teja, S. Kolb, P. Colonna, et al., Angew. Chem. Int. Ed. 63 (2024) e202410162. doi: 10.1002/anie.202410162
52. [52]
  J. Dey, S. Kaltenberger, M. van Gemmeren, Angew. Chem. Int. Ed. 63 (2024) e202404421. doi: 10.1002/anie.202404421
53. [53]
  J. Kong, Z.J. Jiang, J. Xu, et al., J. Org. Chem. 86 (2021) 13350–13359. doi: 10.1021/acs.joc.1c01411
54. [54]
  Q.K. Kang, Y. Li, K. Chen, et al., Angew. Chem. Int. Ed. 61 (2022) e202117381. doi: 10.1002/anie.202117381
55. [55]
  C.P. Lenges, P.S. White, M. Brookhart, J. Am. Chem. Soc. 121 (1999) 4385–4396. doi: 10.1021/ja984409o
56. [56]
  J.L. Rhinehart, K.A. Manbeck, S.K. Buzak, et al., Organometallics 31 (2012) 1943–1952. doi: 10.1021/om2012419
57. [57]
  S.C. Schou, J. Labelled Compd. Radiopharm. 52 (2009) 376–381. doi: 10.1002/jlcr.1612
58. [58]
  A.L. Garreau, H. Zhou, M.C. Young, Org. Lett. 21 (2019) 7044–7048. doi: 10.1021/acs.orglett.9b02618
59. [59]
  W. Peng, Q. Liu, F. Yin, et al., RSC Adv. 11 (2021) 8356–8361. doi: 10.1039/d1ra00236h
60. [60]
  M.H.G. Prechtl, M. Hölscher, Y. Ben-David, et al., Angew. Chem. Int. Ed. 46 (2007) 2269–2272. doi: 10.1002/anie.200603677
61. [61]
  Q. Chen, Q. Liu, J. Xiao, X. Leng, L. Deng, J. Am. Chem. Soc. 143 (2021) 19956–19965. doi: 10.1021/jacs.1c10071
62. [62]
  S. Kopf, F. Ye, H. Neumann, M. Beller, Chem. Eur. J. 27 (2021) 9768–9773. doi: 10.1002/chem.202100468
63. [63]
  G. Pieters, C. Taglang, E. Bonnefille, et al., Angew. Chem. Int. Ed. 53 (2014) 230–234. doi: 10.1002/anie.201307930
64. [64]
  E. Bresó-Femenia, C. Godard, C. Claver, B. Chaudret, S. Castillón, Chem. Commun. 51 (2015) 16342–16345. doi: 10.1039/C5CC06984J
65. [65]
  Z.J. Jiang, S.H. Xu, Y. Su, et al., Chem. Commun. 60 (2024) 384–387. doi: 10.1039/d3cc05257e
66. [66]
  C. Zarate, H. Yang, M.J. Bezdek, D. Hesk, P.J. Chirik, J. Am. Chem. Soc. 141 (2019) 5034–5044. doi: 10.1021/jacs.9b00939
67. [67]
  S. Garhwal, A. Kaushansky, N. Fridman, L.J.W. Shimon, G. de Ruiter, J. Am. Chem. Soc. 142 (2020) 17131–17139. doi: 10.1021/jacs.0c07689
68. [68]
  J. Corpas, P. Viereck, P.J. Chirik, ACS Catal. 10 (2020) 8640–8647. doi: 10.1021/acscatal.0c01714
69. [69]
  H. Xu, Z.J. Jiang, Y. Jia, et al., J. Org. Chem. 89 (2024) 8468–8477. doi: 10.1021/acs.joc.4c00352
70. [70]
  M. Yang, T. Chen, Z.F. Xu, M. Yu, C.Y. Li, Org. Biomol. Chem. 22 (2024) 7596–7600. doi: 10.1039/d4ob01251h
71. [71]
  H. Meng, M.S. Liu, W. Shu, Chem. Sci. 13 (2022) 13690–13707. doi: 10.1039/d2sc04507a
72. [72]
  L. Zhang, T. Ritter, J. Am. Chem. Soc. 144 (2022) 2399–2414. doi: 10.1021/jacs.1c10783
73. [73]
  S.I. Kozhushkov, M. Alcarazo, Eur. J. Inorg. Chem. 2020 (2020) 2486–2500. doi: 10.1002/ejic.202000249
74. [74]
  M.J. Kim, K. Targos, D.E. Holst, D.J. Wang, Z.K. Wickens, Angew. Chem. Int. Ed. 63 (2024) e202314904. doi: 10.1002/anie.202314904
75. [75]
  R. Fan, C. Tan, Y. Liu, et al., Chin. Chem. Lett. 32 (2021) 299–312. doi: 10.1016/j.cclet.2020.06.003
76. [76]
  Á. Péter, G.J.P. Perry, D.J. Procter, Adv. Synth. Catal. 362 (2020) 2135–2142. doi: 10.1002/adsc.202000220
77. [77]
  F. Berger, M.B. Plutschack, J. Riegger, et al., Nature 567 (2019) 223–228. doi: 10.1038/s41586-019-0982-0
78. [78]
  J. Li, J. Chen, R. Sang, et al., Nat. Chem. 12 (2020) 56–62. doi: 10.1038/s41557-019-0353-3
79. [79]
  M.J. Cabrera-Afonso, A. Granados, G.A. Molander, Angew. Chem. Int. Ed. 134 (2022) e202202706. doi: 10.1002/ange.202202706
80. [80]
  D.M. Yan, S.H. Xu, H. Qian, et al., ACS Catal. 12 (2022) 3279–3285. doi: 10.1021/acscatal.2c00638
81. [81]
  E.M. Alvarez, T. Karl, F. Berger, L. Torkowski, T. Ritter, Angew. Chem. Int. Ed. 60 (2021) 13609–13613. doi: 10.1002/anie.202103085
82. [82]
  P.S. Engl, A.P. Häring, F. Berger, et al., J. Am. Chem. Soc. 141 (2019) 13346–13351. doi: 10.1021/jacs.9b07323
83. [83]
  X.Y. Chen, X.X. Nie, Y. Wu, P. Wang, Chem. Commun. 56 (2020) 5058–5061. doi: 10.1039/d0cc00641f
84. [84]
  Y. Wu, Y.H. Huang, X.Y. Chen, Org. Lett. 22 (2020) 6657–6661. doi: 10.1021/acs.orglett.0c02458
85. [85]
  X.X. Nie, Y.H. Huang, P. Wang, Org. Lett. 22 (2020) 7716–7720. doi: 10.1021/acs.orglett.0c02913
86. [86]
  T. Ueda, H. Konishi, K. Manabe, Org. Lett. 14 (2012) 3100–3103. doi: 10.1021/ol301192s
87. [87]
  S.A. Ohnmacht, A.J. Culshaw, M.F. Greaney, Org. Lett. 12 (2010) 224–226. doi: 10.1021/ol902537d
88. [88]
  E.M. Alvarez, M.B. Plutschack, F. Berger, T. Ritter, Org. Lett. 22 (2020) 4593–4596. doi: 10.1021/acs.orglett.0c00982
89. [89]
  N. Kaplaneris, A. Puet, F. Kallert, J. Pöhlmann, L. Ackermann, Angew. Chem. Int. Ed. 62 (2023) e202216661. doi: 10.1002/anie.202216661
90. [90]
  K. Sun, C. Ge, X. Chen, et al., Nat. Commun. 15 (2024) 9693. doi: 10.1038/s41467-024-54079-3
91. [91]
  K. Cheng, E.W. Webb, G.D. Bowden, et al., Org. Lett. 26 (2024) 3419–3423. doi: 10.1021/acs.orglett.4c00929
92. [92]
  X. Kong, Y. Chen, Q. Liu, et al., Org. Lett. 25 (2023) 581–586. doi: 10.1021/acs.orglett.2c03956
93. [93]
  Y.L. Zhang, G.H. Wang, Y. Wu, C.Y. Zhu, P. Wang, Org. Lett. 23 (2021) 8522–8526. doi: 10.1021/acs.orglett.1c03229
94. [94]
  J. Wu, Z. Wang, X.Y. Chen, et al., Sci. China Chem. 63 (2020) 336–340. doi: 10.1007/s11426-019-9652-x
95. [95]
  K. Sun, A. Shi, Y. Liu, et al., Chem. Sci. 13 (2022) 5659–5666. doi: 10.1039/d2sc01241c
96. [96]
  Y. Zhang, S. Xia, W. Shi, et al., Org. Lett. 24 (2022) 7961–7966. doi: 10.1021/acs.orglett.2c03077
97. [97]
  L. Racicot, T. Kasahara, M.A. Ciufolini, Org. Lett. 16 (2014) 6382–6385. doi: 10.1021/ol503177q
98. [98]
  D.Q. Qian, H.J. Shine, J.H. Thurston, K.H. Whitmire, J. Phys. Org. Chem. 16 (2003) 142–147. doi: 10.1002/poc.585
99. [99]
  D.Q. Qian, B. Liu, H.J. Shine, I.Y. Guzman-Jimenez, K.H. Whitmire, J. Phys. Org. Chem. 15 (2002) 139–147. doi: 10.1002/poc.462
100. [100]
  X.Y. Chen, Y.N. Li, Y. Wu, et al., J. Am. Chem. Soc. 145 (2023) 10431–10440. doi: 10.1021/jacs.3c03413
101. [101]
  N. Kim, M. Choi, S.E. Suh, D.M. Chenoweth, Chem. Rev. 124 (2024) 11435–11522. doi: 10.1021/acs.chemrev.4c00296
102. [102]
  J. Shi, L. Li, Y. Li, Chem. Rev. 121 (2021) 3892–4044. doi: 10.1021/acs.chemrev.0c01011
103. [103]
  H. Takikawa, A. Nishii, T. Sakai, K. Suzuki, Chem. Soc. Rev. 47 (2018) 8030–8056. doi: 10.1039/c8cs00350e
104. [104]
  K. Kamikawa, Nat. Rev. Chem. 7 (2023) 496–510. doi: 10.1038/s41570-023-00485-y
105. [105]
  J. Shi, Y. Li, Y. Li, Chem. Soc. Rev. 46 (2017) 1707–1719. doi: 10.1039/C6CS00694A
106. [106]
  J. Tan, X. Feng, R. Fan, Z. Zhuang, Y. Guo, Synlett 34 (2023) 2379–2387. doi: 10.1055/s-0042-1751476
107. [107]
  D.B. Werz, A.T. Biju, Angew. Chem. Int. Ed. 59 (2020) 3385–3398. doi: 10.1002/anie.201909213
108. [108]
  S. Yoshida, T. Yano, Y. Misawa, et al., J. Am. Chem. Soc. 137 (2015) 14071–14074. doi: 10.1021/jacs.5b10557
109. [109]
  Y. Guo, Z. Zhuang, X. Feng, et al., Org. Lett. 25 (2023) 7192–7197. doi: 10.1021/acs.orglett.3c02785
110. [110]
  O. Smith, M.J. Hindson, A. Sreenithya, et al., Nat. Synth. 3 (2024) 58–66.
111. [111]
  C. Arakawa, K. Kanemoto, K. Nakai, et al., J. Am. Chem. Soc. 146 (2024) 3910–3919. doi: 10.1021/jacs.3c11524
112. [112]
  J. Chen, S. Liu, S. Su, et al., Sci. Adv. 9 (2023) eadi1370. doi: 10.1126/sciadv.adi1370
113. [113]
  A. Dasgupta, S. Bhattacharjee, Z. Tong, et al., J. Am. Chem. Soc. 146 (2024) 1196–1203. doi: 10.1021/jacs.3c13080
114. [114]
  J. Yao, Z. Zhang, Z. Li, J. Am. Chem. Soc. 146 (2024) 8839–8846. doi: 10.1021/jacs.4c00426
115. [115]
  Y. Li, D. Qiu, R. Gu, et al., J. Am. Chem. Soc. 138 (2016) 10814–10817. doi: 10.1021/jacs.6b06981
116. [116]
  A. Saputra, R. Fan, T. Yao, J. Chen, J. Tan, Adv. Synth. Catal. 362 (2020) 2683–2688. doi: 10.1002/adsc.202000308
117. [117]
  H. Tan, S. Yu, X. Yuan, et al., Nat. Commun. 15 (2024) 3665. doi: 10.1038/s41467-024-47952-8
118. [118]
  G. Pan, M. Pu, H. Wang, et al., J. Am. Chem. Soc. 145 (2023) 26318–26327. doi: 10.1021/jacs.3c09594
119. [119]
  T. Sephton, A. Charitou, C. Trujillo, et al., Angew. Chem. Int. Ed. 62 (2023) e202310583. doi: 10.1002/anie.202310583
120. [120]
  J.K. Xu, S.J. Li, H.Y. Wang, W.C. Xu, S.K. Tian, Chem. Commun. 53 (2017) 1708–1711. doi: 10.1039/C6CC09311F
121. [121]
  F. Luo, C.L. Li, P. Ji, et al., Chem 9 (2023) 2620–2636. doi: 10.1016/j.chempr.2023.05.032
122. [122]
  T.R. Hoye, B. Baire, D. Niu, P.H. Willoughby, B.P. Woods, Nature 490 (2012) 208–212. doi: 10.1038/nature11518
123. [123]
  D. Niu, P.H. Willoughby, B.P. Woods, B. Baire, T.R. Hoye, Nature 501 (2013) 531–534. doi: 10.1038/nature12492
124. [124]
  S.K. Thompson, T.R. Hoye, J. Am. Chem. Soc. 141 (2019) 19575–19580. doi: 10.1021/jacs.9b11243
125. [125]
  J. Liu, J. Li, B. Ren, et al., Adv. Synth. Catal. 363 (2021) 4734–4739. doi: 10.1002/adsc.202100697
126. [126]
  K.A. Spence, J.V. Chari, M.D. Niro, et al., Chem. Sci. 13 (2022) 5884–5892. doi: 10.1039/d2sc01788a
127. [127]
  J.V. Chari, K.A. Spence, R.B. Susick, N.K. Garg, Nat. Commun. 12 (2021) 3706. doi: 10.1038/s41467-021-23970-8
128. [128]
  Y. Guo, J. Su, J. Xu, Q. Song, Org. Lett. 25 (2023) 6459–6463. doi: 10.1021/acs.orglett.3c01938
129. [129]
  J. Shi, L. Li, C. Shan, et al., J. Am. Chem. Soc. 143 (2021) 2178–2184. doi: 10.1021/jacs.0c11119
130. [130]
  Z. Liu, R.C. Larock, J. Am. Chem. Soc. 127 (2005) 13112–13113. doi: 10.1021/ja054079p
131. [131]
  F.L. Liu, J.R. Chen, Y.Q. Zou, Q. Wei, W.J. Xiao, Org. Lett. 16 (2014) 3768–3771. doi: 10.1021/ol501638x
132. [132]
  D. Kaiser, I. Klose, R. Oost, J. Neuhaus, N. Maulide, Chem. Rev. 119 (2019) 8701–8780. doi: 10.1021/acs.chemrev.9b00111
133. [133]
  H. Yorimitsu, Chem. Rec. 21 (2021) 3356–3369. doi: 10.1002/tcr.202000172
134. [134]
  T. Matsuzawa, T. Hosoya, S. Yoshida, Chem. Sci. 11 (2020) 9691–9696. doi: 10.1039/d0sc04450d
135. [135]
  R. Fan, S. Liu, Q. Yan, et al., Chem. Sci. 14 (2023) 4278–4287. doi: 10.1039/d3sc00072a
136. [136]
  L. Shang, Y. Chang, F. Luo, et al., J. Am. Chem. Soc. 139 (2017) 4211–4217. doi: 10.1021/jacs.7b00969
137. [137]
  Z. Zhang, Z. Sheng, W. Yu, et al., Nature Chem. 9 (2017) 970–976. doi: 10.1038/nchem.2789
138. [138]
  M.H. Aukland, M. Šiauciulis, A. West, G.J.P. Perry, D.J. Procter, Nat. Catal. 3 ˇ (2020) 163–169. doi: 10.1038/s41929-019-0415-3
139. [139]
  D.E. Holst, D.J. Wang, M.J. Kim, I.A. Guzei, Z.K. Wickens, Nature 596 (2021) 74–79. doi: 10.1038/s41586-021-03717-7
140. [140]
  X. Xiao, J. Zeng, J. Fang, et al., J. Am. Chem. Soc. 142 (2020) 5498–5503. doi: 10.1021/jacs.0c00447
141. [141]
  R.A. Roberts, B.E. Metze, A. Nilova, D.R. Stuart, J. Am. Chem. Soc. 145 (2023) 3306–3311. doi: 10.1021/jacs.2c13007
142. [142]
  J.M. Medina, J.L. Mackey, N.K. Garg, K.N. Houk, J. Am. Chem. Soc. 136 (2014) 15798–15805. doi: 10.1021/ja5099935
143. [143]
  Y.F. Yao, J.W. Song, C.P. Zhang, Org. Biomol. Chem. 22 (2024) 7866–7873. doi: 10.1039/d4ob01220h
144. [144]
  J.W. Song, F. Xia, X.L. Zhang, C.P. Zhang, Org. Chem. Front. 11 (2024) 4219–4230. doi: 10.1039/d4qo00618f
145. [145]
  Z. Tan, H. Zhang, K. Xu, C. Zeng, Sci. China Chem. 67 (2024) 450–470. doi: 10.1007/s11426-023-1735-x
146. [146]
  J. Li, S. Zhang, K. Xu, Chin. Chem. Lett. 32 (2021) 2729–2735. doi: 10.1016/j.cclet.2021.03.027
147. [147]
  S. Tang, Y. Liu, A. Lei, Chem 4 (2018) 27–45. doi: 10.1016/j.chempr.2017.10.001
148. [148]
  M. Yan, Y. Kawamata, P.S. Baran, Chem. Rev. 117 (2017) 13230–13319. doi: 10.1021/acs.chemrev.7b00397
149. [149]
  A. Bhunia, T. Kaicharla, D. Porwal, R.G. Gonnade, A.T. Biju, Chem. Commun. 50 (2014) 11389–11392. doi: 10.1039/C4CC05420B
150. [150]
  M. Berchel, P.A. Jaffrès, Chapter 2 - recent developments in phosphonium chemistry, in: V. Iaroshenko (Ed.), Organophosphorus Chemistry: From Molecules to Applications, Wiley-VCH, Weinheim, 2019, pp. 59–111.
151. [151]
  L.K. Hwang, Y. Na, J. Lee, Y. Do, S. Chang, Angew. Chem. Int. Ed. 44 (2005) 6166–6169. doi: 10.1002/anie.200501582
152. [152]
  Y. Toda, S. Gomyou, S. Tanaka, et al., Org. Lett. 19 (2017) 5786–5789. doi: 10.1021/acs.orglett.7b02722
153. [153]
  D.I. Bugaenko, A.A. Volkov, M.V. Livantsov, M.A. Yurovskaya, A.V. Karchava, Chem. Eur. J. 25 (2019) 12502–12506. doi: 10.1002/chem.201902955
154. [154]
  W. Liu, H. Hou, H. Jing, et al., Org. Lett. 25 (2023) 8350–8355. doi: 10.1021/acs.orglett.3c03473
155. [155]
  A.F. Fearnley, J. An, M. Jackson, P. Lindovska, R.M. Denton, Chem. Commun. 52 (2016) 4987–4990. doi: 10.1039/C6CC00556J
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20. [20]
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