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2024 , Vol. 44 >Issue 2: 421 - 437

DOI: https://doi.org/10.6023/cjoc202308007

综述与进展

三芳基碳正离子在有机合成中的应用

  • 李路瑶 ,
  • 贺忠文 ,
  • 张振国 ,
  • 贾振华 ,
  • 罗德平
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  • a 河南工业大学前沿交叉科学与技术学院 郑州 450001
    b 南洋理工大学物理与数学科学学院 化学与生物化学系 新加坡 637371

收稿日期: 2023-08-09

  修回日期: 2023-10-08

  网络出版日期: 2023-10-30

基金资助

河南工业大学高层次人才科研启动基金(31401503)

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Application of Triaryl Carbenium in Organic Synthesis

  • Luyao Li ,
  • Zhongwen He ,
  • Zhenguo Zhang ,
  • Zhenhua Jia ,
  • Teck-Peng Loh
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  • a College of Advanced Interdisciplinary Science and Technology, Henan University of Technology, Zhengzhou 450001
    b Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371
* Corresponding authors. E-mail: ;

Received date: 2023-08-09

  Revised date: 2023-10-08

  Online published: 2023-10-30

Supported by

Start-Up Grant of Henan University of Technology(31401503)

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摘要

三芳基碳正离子作为一种优异的路易斯酸, 其最低空分子轨道(LUMO)轨道能级较低, 易接受一对电子, 被广泛应用于合成转化中, 是重要的试剂和催化剂. 近年来, 三芳基碳正离子在有机合成中主要被用作催化剂、预催化剂、共催化剂和添加剂. 此外, 三芳基碳正离子作为关键中间体, 可以成功应用于四芳基甲烷的合成. 综述了近年来三芳基碳正离子在有机合成中的应用进展, 并总结了三芳基碳正离子在有机合成中的多种功能作用, 希望引起广泛的关注.

关键词： 三芳基碳正离子; 催化剂; 有机合成; 无金属

本文引用格式

李路瑶 , 贺忠文 , 张振国 , 贾振华 , 罗德平 . 三芳基碳正离子在有机合成中的应用[J]. 有机化学, 2024 , 44(2) : 421 -437 . DOI: 10.6023/cjoc202308007

Abstract

Triaryl carbenium, known as an exceptional Lewis acid, possesses a low-lying lowest unoccupied molecular orbital (LUMO) that readily accepts an electron pair, which was widely used in synthetic transformations serving as reagent or catalyst. Over the past decade, triaryl carbenium has been used as catalyst, pre-catalyst, co-catalyst and additive in organic synthesis. Moreover, triaryl carbenium as a key intermediate approached to the successful synthesis of tetra-arylmethane. In this review, the application progress of triaryl carbenium in organic synthesis in recent years is summarized, and its diverse functional roles in organic synthesis are summarized, hoping to attract widespread attention.

Key words： triaryl carbenium; catalysis; organic synthesis; metal-free

参考文献

[1]
(a) Norris J. F. Am. Chem. J. 1901, 25, 117.
[1]
(b) Kehrmann, F.; Wentzel, F. Ber. Dtsch. Chem. Ges. 1901, 34, 3815.
[2]
(a) Mukaiyama, T.; Kobayashi, S.; Shoda S.-I. Chem. Lett. 1984, 13, 907.
[2]
(b) Mukaiyama, T.; Kobayashi, S.; Shoda, S.-I. Chem. Lett. 1984, 13, 1529.
[2]
(c) Mukaiyama, T.; Kobayashi, S.; Murakami, M. Chem. Lett. 1984, 13, 1759.
[3]
Cao, D.; Pan, P.; Li, C.-J.; Zeng, H. Green Synth. Catal. 2021, 2, 303.
[4]
Chen, P.; Tang, X.; Meng, X.; Tang, H.; Pan, Y.; Liang, Y. Green Synth. Catal. 2022, 3, 162.
[5]
Zhou, X.; Zhang, N.; Li, Y.; Mo, Z.; Ma, X.; Chen, Y.; Xu, Y. Green Synth. Catal. 2021, 2, 397.
[6]
Shi, L.; Li, T.; Mei, G. J. Green Synth. Catal. 2022, 3, 227.
[7]
Kang, M. S.; Xin Khoo, J. Y.; Jia, Z.; Loh, T.-P. Green Synth. Catal. 2022, 3, 309.
[8]
Lang, Y.; Han, X.; Peng, X.; Zheng, Z.; Li, C.; Zeng, H. Green Synth. Catal. 2022, 3, 373.
[9]
Lu, S.-N.; Zhang, J.; Li, J.; Chen, Z.; Wu, X. F. Green Synth. Catal. 2022, 3, 385.
[10]
Bah, J.; Franzén, J. Chem.-Eur. J. 2014, 20, 1066.
[11]
Bah, J.; Naidu, V. R.; Teske, J.; Franzén, J. Adv. Synth. Catal. 2015, 357, 148.
[12]
Remaily, M. A. E. A. A. A. E.; Naidu, V. R.; Ni, S.; Franzén, J. Eur. J. Org. Chem. 2015, 47, 6610.
[13]
Naidu, V. R.; Bah, J.; Franzén, J. Eur. J. Org. Chem. 2015, 8, 1834.
[14]
Ni, S.; Remaily, M. A. E. A. A. A. E.; Franzén, J. Adv. Synth. Catal. 2018, 360, 4197.
[15]
Shang, W.; Duan, D.; Liu, Y.; Lv, J. Org. Lett. 2019, 21, 8013.
[16]
Song, R.; Zhuo, C.; Si, W.; Wu, X.; Guan, T.; Yang, D.; Lv, J. Adv. Synth. Catal. 2022, 364, 4069.
[17]
Liu, R.; Wei, Y.; Shi, M. Chin. J. Chem. 2020, 38, 947.
[18]
Nagamalla, S.; Mague J. T. Sathyamoorthi S. Org. Lett. 2022, 24, 939.
[19]
Nagamalla, S.; Paul, D.; Mague, J. T.; Sathyamoorthi, S. Org. Lett. 2022, 24, 6202.
[20]
Xu, Y.; Wang, L.; Chen, C.; Huang, P.; Dai, H.; Jiang, W.; Zhou, Y. Macromolecule. 2023, 56, 501.
[21]
Nomoto, Y.; Horinouchi, R.; Nishiyama, N.; Nakano, K.; Ichikawa, Y.; Kotsuki, H. Synlet. 2017, 28, 265.
[22]
Zhang, Q.; Lv, J.; Li, S.; Luo, S. Org. Lett. 2018, 20, 2269.
[23]
Jin, H.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. ACS Catal. 2019, 9, 11663.
[24]
Zhu, W.; Sun, Q.; Wang, Y.; Yuan, D.; Yao, Y. Org. Lett. 2018, 20, 3101.
[25]
Gan, Z.; Cui, D.; Zhang, H.; Feng, Y.; Huang, L.; Gui, Y.; Gao, L.; Song, Z. Molecule. 2022, 27, 4730.
[26]
(a) Riant, O.; Samuel, O.; Kagan, H. B. J. Am. Chem. Soc. 1993, 115, 5835.
[26]
(b) Taudien, S.; Riant, O.; Kagan, H. Tetrahedron Lett. 1995, 36, 3513.
[26]
(c) Sammakia, T.; Latham, H. A. Tetrahedron Lett. 1995, 36, 6867.
[26]
(d) Chen, C.-T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341.
[26]
(e) Magdziak, D.; Pettus, L. H.; Pettus, T. R. R. Org. Lett. 2001, 3, 557.
[26]
(f) Bjurling, E.; Berg, U.; Andersson, C.-M. Organometallic. 2002, 21, 1583.
[27]
Lv, J.; Zhang, Q.; Zhong, X.; Luo, S. J. Am. Chem. Soc. 2015, 137, 15576.
[28]
Zhang, Q.; Lv, J.; Luo, S. Beilstein J. Org. Chem. 2019, 15, 1304.
[29]
Cai, X.; Keshavarz, A.; Omaque, J. D.; Stokes, B. J. Org. Lett. 2017, 19, 2626.
[30]
Popov, S.; Shao, B.; Bagdasarian, A. L.; Benton, T. R.; Zou, L.; Yang, Z.; Houk, K. N.; Nelson, H. M. Scienc. 2018, 361, 381.
[31]
Wigman, B.; Popov, S.; Bagdasarian, A. L.; Shao, B.; Benton T. R. Williams, C. G.; Fisher, S. P.; Lavallo, V.; Houk, K. N.; Nelson, H. M. J. Am. Chem. Soc. 2019, 141, 9140.
[32]
Zhang, Z.; Ji, L.; Liu, X.; Li, Z.; Lv, Y.; Jia, Z.; Loh, T.-P. Org. Chem. Front. 2022, 9, 5154.
[33]
Zhang, Z.; Liu, X.; Ji, L.; Zhang, T.; Jia, Z.; Loh, T.-P. ACS Catal. 2022, 12, 2052.
[34]
Zhang, Z.; Gu, J.; Lv, Y.; Ji, L.; Liu, X.; Wu, B.; Liu, F.; Jia, Z.; Loh, T.-P. Cell Rep. Phys. Sci. 2023, 4, 101246.
[35]
(a) Shi, X.; Nishiura, M.; Hou, Z. Angew. Chem.. Int. Ed. 2016, 55, 14812.
[35]
(b) Wang, H.; Zhao, Y.; Nishiura, M.; Yang, Y.; Luo, G.; Luo, Y.; Hou, Z. J. Am. Chem. Soc. 2019, 141, 12624.
[35]
(c) Wang, H.; W, X.; Yang, Y.; Nishiura, M.; Hou, Z. Angew. Chem.. Int. Ed. 2020, 59, 7173.
[35]
(d) Guo, F.; Jiang, L.; Diao, K.; Hou, Z. Polym. Chem. 2020, 11, 1314.
[36]
Song, G.; Luo, G.; Oyamada, J.; Luo, Y.; Hou, Z. Chem. Sci. 2016, 7, 5265.
[37]
Luo, Y.; Teng, H.-L.; Nishiura, M.; Hou, Z. Angew. Chem.. Int. Ed. 2017, 56, 9207.
[38]
Arii, H.; Nakabayashi, K.; Mochida, K.; Kawashima, T. Molecule. 2016, 21, 999.
[39]
Forster, F.; Rendo?n Lo?pez, V. M.; Oestreich, M. Organometallic. 2018, 37, 2656.
[40]
He, T.; Wang, G.; Bonetti, V.; Klare, H. F. T.; Oestreich, M. Angew. Chem.. Int. Ed. 2020, 59, 12186.
[41]
He, T.; Wang, G.; Long, P.-W.; Kemper, S.; Irran, E.; Klare, H. F. T.; Oestreich, M. Chem. Sci. 2021, 12, 569.
[42]
Roy, A.; Gao, H.; Klare, H. F. T.; Oestreich, M. Synthesi. 2023, 55, 1602.
[43]
Laye, C.; Lusseau, J.; Robert, F.; Landais, Y. Adv. Synth. Catal. 2021, 363, 3035.
[44]
Israr, M.; Bae, H. Y. Green Chem. 2023, 25, 2387.
[45]
Courant, T.; Lombard, M.; Boyarskaya, D. V.; Neuville, L.; Masson, G. Org. Biomol. Chem. 2020, 18, 6502.
[46]
Yoshida, S.; Shimomori, K.; Kim, Y.; Hosoya, T. Angew. Chem.. Int. Ed. 2016, 55, 10406.
[47]
Idogawa, R.; Kim, Y.; Shimomori, K.; Hosoya, T.; Yoshida, S. Org. Lett. 2020, 22, 9292.
[48]
Li, X.; Duan, M.; Deng, Z.; Shao, Q.; Chen, M.; Zhu, G.; Houk, K. N.; Sun, J. Nat. Catal. 2020, 3, 1010.
[49]
Tan, X.; Deng, Z.; Wang, Q.; Chen, S.; Zhu, G.; Sun, J. Nat. Synth. 2023, 2, 275.
[50]
Liu, M.; Shen, B.; Liu, C.; Yu, P.; Li, P. J. Am. Chem. Soc. 2023, 145, 14562.
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