Citation: Wei Xiao, Jie Wu. Recent advance in carbocation-catalyzed reactions[J]. Chinese Chemical Letters, ;2023, 34(2): 107637. doi: 10.1016/j.cclet.2022.06.060 shu

Recent advance in carbocation-catalyzed reactions

Wei Xiao ^a ,
Jie Wu ^{a, b, c, *,}

a.
School of Pharmaceutical and Materials Engineering & Institute for Advanced Studies, Taizhou University, Taizhou 318000, China
b.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
c.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China

jie_wu@fudan.edu.cn

Received Date: 26 April 2022
Revised Date: 14 June 2022
Accepted Date: 21 June 2022
Available Online: 26 June 2022

Figures(37)

Carbocations such as tropylium and trityl cation, can be stable enough to be isolated and used without inert conditions. They can act as Lewis acids to lower the LUMO of electrophile, thus promoting reactions with nucleophiles. Additionally, the interaction between carbocations and alcohols can form Brønsted acids with enhanced acidity. Furthermore, electrophoto activation of TAC⁺ (trisaminocyclopropenium ion) delivers the excited radical dication TAC^•2+*, which is a strong oxidant and capable of oxidizing a range of challenging substrates. Moreover, Pr-DMQA⁺ is disclosed as a versatile photoredox catalyst as its excited state can be quenched through both oxidation and reduction. This review summarizes recent advance in carbocation-catalyzed reactions. These developed methods provide an environmentally friendly pathway for the synthesis of valuable compounds and will inspire chemists to discover more interesting transformations promoted by carbocations.
- Carbocation,
- Lewis acid,
- Photoredox catalysis,
- Tropylium cation,
- Trityl cation
1. [1]
  J. Clayden, N. Greeves, S. Warren, Organic Chemistry, 2^nd Ed., University Press, Oxford, 2012.
2. [2]
  G.A. Olah, G.K.S. Prakash, Carbocation Chemistry, Wiley, Hoboken, 2004.
3. [3]
  G. Merling, Ber. Dtsch. Chem. Ges. 24 (1891) 3108–3126. doi: 10.1002/cber.189102402151
4. [4]
  O. Sereda, S. Tabassum, R. Wilhelm, Top. Curr. Chem. 291 (2010) 349–393.
5. [5]
  H. Yamamoto, Lewis Acids in Organic Synthesis, Wiley-VCH, Weinheim, 2000.
6. [6]
  J.J. Koenig, M. Breugst, Catalysis by Molecular Iodine, in: S. Huber (Ed.), Halogen Bonding in Solution, Wiley-VCH, Weinheim, 2021, pp. 237–268.
7. [7]
  L. Capaldo, L.L. Quadri, D. Ravelli, Angew. Chem. Int. Ed. 58 (2019) 17508–17510. doi: 10.1002/anie.201910348
8. [8]
  L. Mei, T. Gianetti, Synlett 32 (2021) 337–343. doi: 10.1055/s-0040-1705942
9. [9]
  V.R. Naidu, S.J. Ni, J. Franzen, ChemCatChem 7 (2015) 1896–1905. doi: 10.1002/cctc.201500225
10. [10]
  J. Bah, J. Franzen, Chem. Eur. J. 20 (2014) 1066–1072. doi: 10.1002/chem.201304160
11. [11]
  W. Xiao, J. Wu, Chin. Chem. Lett. 32 (2021) 2751–2755. doi: 10.1016/j.cclet.2021.03.033
12. [12]
  D.J.M. Lyons, R.D. Crocker, D. Enders, T.V. Nguyen, Green Chem. 19 (2017) 3993–3996. doi: 10.1039/C7GC01519D
13. [13]
  P. Pommerening, J. Mohr, J. Friebel, M. Oestreich, Eur. J. Org. Chem. 2017 (2017) 2312–2316. doi: 10.1002/ejoc.201700239
14. [14]
  Q.C. Zhang, J. Lv, S.J. Li, S.Z. Luo, Org. Lett. 20 (2018) 2269–2272. doi: 10.1021/acs.orglett.8b00619
15. [15]
  Q. Zhang, J. Lv, S. Luo, Beilstein J. Org. Chem. 15 (2019) 1304–1312. doi: 10.3762/bjoc.15.129
16. [16]
  U.P.N. Tran, G. Oss, D.P. Pace, J. Ho, T.V. Nguyen, Chem. Sci. 9 (2018) 5145–5151. doi: 10.1039/C8SC00907D
17. [17]
  S.J. Ni, J. Franzen, Chem. Commun. 54 (2018) 12982–12985. doi: 10.1039/C8CC06734A
18. [18]
  S.J. Ni, M. El Remaily, J. Franzen, Adv. Synth. Catal. 360 (2018) 4197–4204. doi: 10.1002/adsc.201800788
19. [19]
  M.A. Hussein, V.T. Huynh, R. Hommelsheim, R.M. Koenigs, T.V. Nguyen, Chem. Commun. 54 (2018) 12970–12973. doi: 10.1039/C8CC07329E
20. [20]
  W.S. Shang, D.P. Duan, Y.J. Liu, J. Lv, Org. Lett. 21 (2019) 8013–8017. doi: 10.1021/acs.orglett.9b03005
21. [21]
  S.H. Doan, M.A. Hussein, T.V. Nguyen, Chem. Commun. 57 (2021) 8901–8904. doi: 10.1039/D1CC02947A
22. [22]
  P.K. Ranga, F. Ahmad, P. Nager, et al., J. Org. Chem. 86 (2021) 4994–5010. doi: 10.1021/acs.joc.0c02940
23. [23]
  M. Rezazadeh Khalkhali, M.M.D. Wilde, M. Gravel, Org. Lett. 23 (2021) 155–159. doi: 10.1021/acs.orglett.0c03879
24. [24]
  S. Sharma Rekha, G. Singh, R. Vijaya Anand, ACS Org. Inorg. Au 2 (2022) 186–196. doi: 10.1021/acsorginorgau.1c00033
25. [25]
  J.J. Liu, J.X. Xu, Z.J. Li, et al., Eur. J. Org. Chem. 2017 (2017) 3996–4003. doi: 10.1002/ejoc.201700634
26. [26]
  W.J. Patterson, K. Lucas, V.A. Jones, et al., Eur. J. Org. Chem. 2021 (2021) 6737–6742. doi: 10.1002/ejoc.202100946
27. [27]
  W.G. Zhu, Q. Sun, Y.R. Wang, D. Yuan, Y.M. Yao, Org. Lett. 20 (2018) 3101–3104. doi: 10.1021/acs.orglett.8b01158
28. [28]
  G. Oss, J. Ho, N. Thanh Vinh, Eur. J. Org. Chem. 2018 (2018) 3974–3981. doi: 10.1002/ejoc.201800579
29. [29]
  P. Goswami, S. Sharma, G. Singh, et al., J. Org. Chem. 83 (2018) 4213–4220. doi: 10.1021/acs.joc.8b00225
30. [30]
  H.M. Jin, M. Rudolph, F. Rominger, A.S.K. Hashmi, ACS Catal. 9 (2019) 11663–11668. doi: 10.1021/acscatal.9b03911
31. [31]
  Y.A. Rulev, Z.T. Gugkaeva, A.V. Lokutova, et al., ChemSusChem 10 (2017) 1152–1159. doi: 10.1002/cssc.201601246
32. [32]
  K. Omoregbee, K.N.H. Luc, A.H. Dinh, T.V. Nguyen, J. Flow Chem. 10 (2020) 161–166. doi: 10.1007/s41981-020-00082-w
33. [33]
  J. Xu, Y. Gao, Z. Li, et al., Eur. J. Org. Chem. 2020 (2020) 311–315. doi: 10.1002/ejoc.201901537
34. [34]
  H. Huang, Z.M. Strater, M. Rauch, et al., Angew. Chem. Int. Ed. 58 (2019) 13318–13322. doi: 10.1002/anie.201906381
35. [35]
  H. Huang, Z.M. Strater, T.H. Lambert, J. Am. Chem. Soc. 142 (2020) 1698–1703. doi: 10.1021/jacs.9b11472
36. [36]
  T. Shen, T.H. Lambert, Science 371 (2021) 620–626. doi: 10.1126/science.abf2798
37. [37]
  T. Shen, T.H. Lambert, J. Am. Chem. Soc. 143 (2021) 8597–8602. doi: 10.1021/jacs.1c03718
38. [38]
  H. Huang, T.H. Lambert, J. Am. Chem. Soc. 143 (2021) 7247–7252. doi: 10.1021/jacs.1c01967
39. [39]
  W. Xiao, X. Wang, R. Liu, J. Wu, Chin. Chem. Lett. 32 (2021) 1847–1856. doi: 10.1016/j.cclet.2021.02.009
40. [40]
  W. Xiao, J. Wu, Chin. Chem. Lett. 31 (2020) 3083–3094. doi: 10.1016/j.cclet.2020.07.035
41. [41]
  L. Mei, J.M. Veleta, T.L. Gianetti, J. Am. Chem. Soc. 142 (2020) 12056–12061. doi: 10.1021/jacs.0c05507
42. [42]
  L. Mei, J. Moutet, S.M. Stull, T.L. Gianetti, J. Org. Chem. 86 (2021) 10640–10653. doi: 10.1021/acs.joc.1c01313
43. [43]
  S.M. Stull, L. Mei, T.L. Gianetti, Synlett 33 (2022) 1194–1198. doi: 10.1055/a-1665-9220
44. [44]
  R. Mir, T. Dudding, J. Org. Chem. 82 (2017) 709–714. doi: 10.1021/acs.joc.6b02733
45. [45]
  K. Dempsey, R. Mir, I. Smajlagic, et al., Tetrahedron 74 (2018) 3507–3511. doi: 10.1016/j.tet.2018.04.083
46. [46]
  T. Courant, M. Lombard, D.V. Boyarskaya, L. Neuville, G. Masson, Org. Bio. Chem. 18 (2020) 6502–6508. doi: 10.1039/D0OB01502D
47. [47]
  N.N.H. Ton, B.K. Mai, T.V. Nguyen, J. Org. Chem. 86 (2021) 9117–9133. doi: 10.1021/acs.joc.1c01208
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