Chinese Journal of Organic Chemistry >
Research Progress in Benzene-Forming Cyclotrimerization Reactions
Received date: 2024-07-31
Revised date: 2024-08-24
Online published: 2024-09-02
Supported by
National Natural Science Foundation of China(22271047); Natural Science Foundation of Fujian Province(2022J011121)
Benzene-forming cyclotrimerization reactions are capable of constructing cyclic structures via continuous transformation of three identical functional groups, and have applications in various fields such as natural product synthesis, polymer chemistry, supramolecular chemistry, and material science. In this review, the recent advances in cyclotrimerization reactions forming a central benzene ring are systematically summarized according to the different reaction types of functional groups. In each typical example, the reaction conditions, mechanism, possible side reactions, and applications are discussed. A future perspective on benzene-forming cyclotrimerization reactions is also presented.
Cen Zhou , Xin Zhao , Xiao Zhang . Research Progress in Benzene-Forming Cyclotrimerization Reactions[J]. Chinese Journal of Organic Chemistry, 2025 , 45(1) : 42 -55 . DOI: 10.6023/cjoc202407048
| [1] | Berthelot, M. Liebigs Ann. Chem. 1866, 139, 272. |
| [2] | Reppe, W.; Schlichting, O.; Klager, K.; Toepel, T. Liebigs Ann. Chem. 1948, 560, 1. |
| [3] | Furlani Donda, A.; Cervone, E.; Biancifiori, M. A. Recl. Trav. Chim. Pays-Bas 1962, 81, 585. |
| [4] | Cheng, J.-S.; Jiang, H.-F.; Zhang, Q.-J.; Ouyang, X.-Y. Chin. J. Org. Chem. 2003, 23, 313 (in Chinese). |
| [4] | (程金生, 江焕峰, 张群健, 欧阳小月, 有机化学, 2003, 23, 313.) |
| [5] | Roglans, A.; Pla-Quintana, A.; Solà, M. Chem. Rev. 2021, 121, 1894. |
| [6] | Sugahara, T.; Guo, J.-D.; Sasamori, T.; Nagase, S.; Tokitoh, N. Angew. Chem., Int. Ed. 2018, 57, 3499. |
| [7] | Yamamoto, K.; Nagae, H.; Tsurugi, H.; Mashima, K. Dalton Trans., 2016, 45, 17072. |
| [8] | Hapke, M. Tetrahedron Lett. 2016, 57, 5719. |
| [9] | Yang, J. C.; Verkade, J. G. J. Am. Chem. Soc. 1998, 120, 6834. |
| [10] | Neumeier, M.; Chakraborty, U.; Schaarschmidt, D.; de la Pena O'Shea, V.; Perez-Ruiz, R.; Jacobi von Wangelin, A. Angew. Chem., nt. Ed. 2020, 59, 13473. |
| [11] | Ouchi, S.; Inoue, T.; Nogami, J.; Nagashima, Y.; Tanaka, K. Nat. Synth. 2023, 2, 535. |
| [12] | Liang, K.; Lu, L.; Liu, X.; Yang, D.; Wang, S.; Gao, Y.; Alhumade, H.; Yi, H.; Lei, A. ACS Catal. 2021, 11, 14892. |
| [13] | Arepally, S.; Nandhakumar, P.; González-Montiel, G. A.; Dzhaparova, A.; Kim, G.; Ma, A.; Nam, K. M.; Yang, H.; Cheong, P. H.-Y.; Park, J. K. ACS Catal. 2022, 12, 6874. |
| [14] | Ardizzoia, G. A.; Brenna, S.; Cenini, S.; La Monica, G.; Masciocchi, N.; Maspero, A. J. Mol. Catal. A: Chem. 2003, 204-205, 333. |
| [15] | Haley, R. A.; Zellner, A. R.; Krause, J. A.; Guan, H.; Mack, J. ACS Sustainable Chem. Eng. 2016, 4, 2464. |
| [16] | Hollingsworth, R. L.; Bheemaraju, A.; Lenca, N.; Lord, R. L.; Groysman, S. Dalton Trans. 2017, 46, 5605. |
| [17] | Xu, Y.; Pan, Y.; Wu, Q.; Wang, H.; Liu, P. J. Org. Chem. 2011, 76, 8472. |
| [18] | Huang, Y.-S.; Huang, G.-T.; Liu, Y.-L.; Yu, J.-S. K.; Tsai, Y.-C. Angew. Chem., nt. Ed. 2017, 56, 15427. |
| [19] | Doll, J. S.; Eichelmann, R.; Hertwig, L. E.; Bender, T.; Kohler, V. J.; Bill, E.; Wadepohl, H.; Roşca, D.-A. ACS Catal. 2021, 11, 5593. |
| [20] | Sen, A.; Sato, T.; Ohno, A.; Baek, H.; Muranaka, A.; Yamada, Y. M. A. JACS Au 2021, 1, 2080. |
| [21] | Fan, J.-T.; Fan, X.-H.; Gao, C.-Y.; Wei, J.; Yang, L.-M. Org. Chem. Front. 2022, 9, 2357. |
| [22] | Peña, D.; Escudero, S.; Pérez, D.; Guitián, E.; Castedo, L. Angew. Chem., nt. Ed. 1998, 37, 2659. |
| [23] | Pozo, I.; Guitián, E.; Pérez, D.; Peña, D. Acc. Chem. Res. 2019, 52, 2472. |
| [24] | Guo, C.; Xia, D.; Yang, Y.; Zuo, X. Chem. Rec. 2019, 19, 1. |
| [25] | Seyler, H.; Purushothaman, B.; Jones, D. J.; Holmes, A. B.; Wong, W. W. H. Pure Appl. Chem. 2012, 84, 1047. |
| [26] | Hayase, N.; Miyauchi, Y.; Aida, Y.; Sugiyama, H.; Uekusa, H.; Shibata, Y.; Tanaka, K. Org. Lett. 2017, 19, 2993. |
| [27] | Hayase, N.; Nogami, J.; Shibata, Y.; Tanaka, K. Angew. Chem.,Int. Ed. 2019, 58, 9439. |
| [28] | Nogami, J.; Nagashima, Y.; Tanaka, Y.; Sugiyama, H.; Uekusa, H.; Muranaka, A.; Uchiyama, M.; Tanaka, K. Angew. Chem.,Int. Ed. 2022, 61, e202200800. |
| [29] | Liu, J.; Zheng, R.; Tang, Y.; Haussler, M.; Lam, J. W. Y; Qin, A.; Ye, M.; Hong, Y.; Gao, P.; Tang, B. Z. Macromolecules 2007, 40, 7473. |
| [30] | Yuan, S.; Dorney, B.; White, D.; Kirklin, S.; Zapol, P.; Yu, L.; Liu, D.-J. Chem. Commun. 2010, 46, 4547. |
| [31] | Wang, Z.; Shi, Y.; Wang, J.; Li, L.; Wu, H.; Yao, B.; Sun, J. Z.; Qin, A.; Tang, B. Z. Polym. Chem. 2014, 5, 5890. |
| [32] | Liu, J.; Ruffieux, P.; Feng, X.; Mu?llen, K.; Fasel, R. Chem. Commun. 2014, 50, 11200. |
| [33] | Pla-Quintana, A.; Roglans, A. Molecules 2010, 15, 9230. |
| [34] | Domínguez, G.; Pérez-Castells, J. Chem. Soc. Rev. 2011, 40, 3430. |
| [35] | Morita, F.; Kishida, Y.; Sato, Y.; Sugiyama, H.; Abekura, M.; Noga- mi, J.; Toriumi, N.; Nagashima, Y.; Kinoshita, T.; Fukuhara, G.; Uchiyama, M., Uekusa, H.; Tanaka, K. Nat. Synth. 2024, 3, 774. |
| [36] | Amick, A. W.; Scott, L. T. J. Org. Chem. 2007, 72, 3412. |
| [37] | Kumar, R.; Chmielewski, P. J.; Lis, T.; Volkmer, D.; Stępień, M. Angew. Chem.,Int. Ed. 2022, 61, e202207486. |
| [38] | Reif, P.; Gupta, N. K.; Rose, M. Green Chem. 2023, 25, 1588. |
| [39] | Deng, K.; Huai, Q.-Y.; Shen, Z.-L.; Li, H.-J.; Liu, C.; Wu, Y.-C. Org. Lett. 2015, 17, 1473. |
| [40] | Adams, R.; Hufferd, R. W. Org. Synth. 1922, 2, 41. |
| [41] | Kotha, S.; Meshram, M.; Panguluri, N.R.; Shah, V.; Todeti, S.; Shirbhate, M. E. Chem. Asian J. 2019, 14, 1356. |
| [42] | Cao, X. Y.; Zhang, W. B.; Wang, J. L.; Zhou, X. H.; Lu, H.; Pei, J. J. Am. Chem. Soc. 2003, 125, 12430. |
| [43] | Dash, B. P.; Satapathy, R.; Maguire, J. A.; Hosmane, N. S. Org. Lett. 2008, 10, 2247. |
| [44] | Dash, B. P.; Satapathy, R.; Gaillard, E. R.; Maguire, J. A.; Hos- mane, N. S. J. Am. Chem. Soc. 2010, 132, 6578. |
| [45] | Goubard, F.; Dumur, F. RSC Adv. 2015, 5, 3521. |
| [46] | Górski, K.; Mech-Piskorz, J.; Pietraszkiewicz, M. New J. Chem. 2022, 46, 8939. |
| [47] | Elmorsy, S. S.; Pelter, A.; Hursthouse, M. B.; Ando, D. Tetrahedron Lett. 1992, 33, 821. |
| [48] | Ginnari-Satriani, L.; Casagrande, V.; Bianco, A.; Ortaggi, G. Org. Biomol. Chem. 2009, 7, 2513. |
| [49] | Scott, L. T.; Boorum, M. M.; McMahon, B. J.; Hagen, S.; Mack, J.; Blank, J.; Wegner, H.; de Meijere, A. Science 2002, 295, 1500. |
| [50] | Pascal, R. A., Jr.; Mathai, M. S.; Shen, X.; Ho, D. M. Angew. Chem., Int. Ed. 2001, 40, 4746. |
| [51] | Song, Q.; Ho, D. M.; Pascal, R. A.,Jr. J. Org. Chem. 2007, 72, 4449. |
| [52] | Alaimo, P. J.; Marshall, A.-L.; Andrews, D. M.; Langenhan, J. M. Org. Synth. 2010, 87, 192. |
| [53] | Sanguinet, L.; Williams, J. C.; Yang, Z.; Twieg, R. J.; Mao, G.; Singer, K. D.; Wiggers, G.; Petschek, R. G. Chem. Mater. 2006, 18, 4259. |
| [54] | Al-Zaydi, K. M.; Nhari, L. M.; Borik, R. M.; Elnagdi, M. H. Green Chem. Lett. Rev. 2010, 3, 93. |
| [55] | Beryozkina, T. V.; Zhidovinov, S. S.; Shafran, Y. M.; Eltsov, O. S.; Slepukhin, P. A.; Leban, J.; Marquez, J.; Bakulev, V. A. Tetrahedron 2014, 70, 3915. |
| [56] | Tuo, D.-H.; He, Q.; Wang, Q.-Q.; Ao, Y.-F.; Wang, D.-X. Chin. J. Chem. 2019, 37, 684. |
| [57] | Kim, T. Y.; Kim, H. S.; Lee, K. Y.; Kim, J. N. Bull. Korean Chem. Soc. 1999, 20, 1255. |
| [58] | Kim, T. Y.; Kim, H. S.; Lee, K. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2000, 21, 521. |
| [59] | Saha, A.; Wu, C. M.; Peng, R.; Koodali, R.; Banerjee, S. Eur. J. Org. Chem. 2019, 104. |
| [60] | Midya, S. P.; Mondal, S.; Islam, A. S. M.; Rashid, A.; Mondal, S.; Paul, A.; Ghosh, P. Org. Lett. 2022, 24, 4438. |
| [61] | Yang, B.; Bjo?rk, J.; Lin, H.; Zhang, X.; Zhang, H.; Li, Y.; Fan, J.; Li, Q.; Chi, L. J. Am. Chem. Soc. 2015, 137, 4904. |
| [62] | Wang, C.; Li, C.; Rutledge, E.; Che, S.; Lee, J.; Kalin, A.; Zhang, C.; Zhou, H.-C.; Guo, Z.-H.; Fang, L. J. Mater. Chem. A 2020, 8, 15891. |
| [63] | Che, S.; Li, C; Wang, C; Zaheer, W.; Ji, X.; Phillips, B.; Gurbandurdyyev, G.; Glynn, J; Guo, Z.-H.; Al-Hashimi, M.; Zhou, H.-C.; Banerjee, S.; Fang, L. Chem. Sci. 2021, 12, 8438. |
| [64] | Sprick, R. S.; Thomas, A.; Scherf, U. Polym. Chem. 2010, 1, 283. |
| [65] | Zhang, Q.; Sun, Y.; Li, H.; Tang, K.; Zhong, Y.-W.; Wang, D.; Guo, Y.; Liu, Y. Research 2021, 9790705. |
| [66] | Zhou, C.; Xuan, W.; Luo, S.-P.; Bao, Y.-H. J. Chem. Res. 2018, 42, 556. |
| [67] | Gassman, P. G.; Gennick, I. J. Am. Chem. Soc. 1980, 102, 6863. |
| [68] | Durr, R.; Cossu, S.; Lucchini, V.; De Lucchi, O. Angew. Chem., Int. Ed. 1997, 36, 2805. |
| [69] | Fabris, F.; De Martin, A.; De Lucchi, O. Tetrahedron Lett. 1999, 40, 9121. |
| [70] | Zonta, C.; Cossu, S.; Peluso, P.; De Lucchi, O. Tetrahedron Lett. 1999, 40, 8185. |
| [71] | Cossu, S.; Cimenti, C.; Peluso, P.; Paulon, A.; De Lucchi, O. Angew. Chem., Int. Ed. 2001, 40, 4086. |
| [72] | Fabris, F.; Bellotto, L.; De Lucchi, O. Tetrahedron Lett. 2003, 44, 1211. |
| [73] | Yan, Z.; McCracken, T.; Xia, S.; Maslak, V.; Gallucci, J.; Hadad, C.; M. Badjić, J. D. J. Org. Chem. 2008, 73, 355. |
| [74] | Wang, M.; Lin, Z. Organometallics 2010, 29, 3077. |
| [75] | Gunther, M. J.; Pavlović, R. Z.; Fernandez, J. P.; Lei, Z.; Gallucci, J.; Hadad, C. M.; Badjić, J. D. J. Org. Chem. 2019, 84, 4392. |
| [76] | Zonta, C.; Cossu, S.; De Lucchi, O. Eur. J. Org. Chem. 2000, 1965. |
| [77] | Zonta, C.; Fabris, F.; De Lucchi, O. Org. Lett. 2005, 7, 1003. |
| [78] | Erdoğan, M.; Eşsiz, S.; Fabris, F.; Daştan, A. ARKIVOC 2018, iii, 134. |
| [79] | Maslak, V.; Yan, Z.; Xia, S.; Gallucci, J.; Hadad, C. M.; Badjć, J. D. J. Am. Chem. Soc. 2006, 128, 5887. |
| [80] | Sakurai, H.; Daiko, T.; Hirao, T. Science 2003, 301, 1878. |
| [81] | Cossu, S.; De Lucchi, O.; Paulon, A.; Peluso, P.; Zonta, C. Tetrahedron Lett. 2001, 42, 3515. |
| [82] | Cossu, S.; De Lucchi, O.; Paulon, A.; Peluso, P.; Zonta, C. Tetrahedron 2001, 57, 8719. |
| [83] | Higashibayashi, S.; Sakurai, H. Chem. Lett. 2007, 36, 18. |
| [84] | Yamanaka, M.; Morishima, M.; Shibata, Y.; Higashibayashi, S.; Sakurai, H. Organometallics 2014, 33, 3060. |
| [85] | Lei, Z.; Gunther, M. J.; Liyana Gunawardana, V. W.; Pavlović, R. Z.; Xie H.; Zhu, X.; Keenan, M.; Riggs, A.; Badjić, J. D. Chem. Commun. 2020, 56, 10243. |
| [86] | Higashibayashi, S.; Sakurai, H. J. Am. Chem. Soc. 2008, 130, 8592. |
| [87] | Tan, O.; Higashibayashi, S.; Karanjit, S.; Hidehiro Sakurai, H. Nat. Commun. 2012, 3, 891. |
| [88] | Paulon, A.; Cossu, S.; De Lucchi, O.; Zonta, C. Chem. Commun. 2000, 1837. |
| [89] | Hermann, K.; Sardini, S.; Ruan, Y.; Yoder, R. J.; Chakraborty, M.; Vyas, S.; Hadad, C. M.; Badjić, J. D. J. Org. Chem. 2013, 78, 2984. |
| [90] | Yamamoto, T.; Hayashi, Y.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1978, 51, 2091. |
| [91] | Zhou, Z.; Yamamoto, T. J. Organomet. Chem. 1991, 414, 119. |
| [92] | Patra, A.; Wijsboom, Y. H.; Shimon, L. J. W.; Bendikov, M. Angew. Chem., Int. Ed. 2007, 46, 8814. |
| [93] | Chen, Q.; Thompson, A. L.; Christensen, K. E.; Horton, P. N.; Coles, S. J.; Anderson, H. L. J. Am. Chem. Soc. 2023, 145, 11859. |
| [94] | Schroeder, Z. W.; LeDrew, J.; Selmani, V. M.; Maly, K. E. RSC Adv. 2021, 11, 39564. |
| [95] | Ru?diger, E. C.; Porz, M.; Schaffroth, M.; Rominger, F.; Bunz, U. H. F. Chem.-Eur. J. 2014, 20, 12725. |
| [96] | Liu, P.; Chen, X.-Y.; Cao, J.; Ruppenthal, L.; Gottfried, J. M.; Müllen, K.; Wang, X.-Y. J. Am. Chem. Soc. 2021, 143, 5314. |
| [97] | Li, Z.-M.; Shuai, B.; Ma, C.; Fang, P.; Mei, T.-S. Chin. J. Chem. 2022, 40, 2335. |
| [98] | Pérez, D.; Guitián, E. Chem. Soc. Rev. 2004, 33, 274. |
| [99] | Voisin, E.; Williams, V. E. Macromolecules 2008, 41, 2994. |
| [100] | Boden, N.; Borner, R. C.; Bushby, R. J.; Cammidge, A. N.; Jesudason, M. V. Liq. Cryst. 1993, 15, 851. |
| [101] | Kumar, S.; Varshney, S. K. Synthesis 2001, 305. |
| [102] | Kumar, S.; Manickam, M. Chem. Commun. 1997, 1615. |
| [103] | Cho, H. Y.; Scott, L. T. Tetrahedron Lett. 2015, 56, 3458. |
| [104] | Regenbrecht, C.; Waldvogel, S. R. Beilstein J. Org. Chem. 2012, 8, 1721. |
| [105] | Nakamura, Y.; Sato, Y.; Shida, N.; Atobe, M. Electrochemistry 2021, 89, 395. |
| [106] | Li, X.-C.; Wang, C.-Y.; Lai, W.-Y.; Huang, W. J. Mater. Chem. C 2016, 4, 10574. |
| [107] | Kaneko, T.; Matsuo, M. Heterocycles 1979, 12, 471. |
| [108] | Mackintosh, J. G.; Mount, A. R. J. Chem. Soc., Faraday Trans. 1994, 90, 1121. |
| [109] | Mackintosh, J. G.; Redpath, C. R.; Jones, A. C.; Langridge-Smith, P. R. R.; Mount, A. R. J. Electroanal. Chem. 1995, 388, 179. |
| [110] | Manini, P.; d’Ischia, M.; Milosa, M.; Prota, G. J. Org. Chem. 1998, 63, 7002. |
| [111] | Greci, L.; Tommasi, G.; Petrucci, R.; Marrosu, G.; Trazza, A.; Sgarabotto, P.; Righi, R.; Alberti, A. J. Chem. Soc., Perkin Trans. 2000, 11, 2337. |
| [112] | Robertson, N.; Parsons, S.; MacLean, E. J.; Coxall, R. A.; Mount, A. R. J. Mater. Chem. 2000, 10, 2043. |
| [113] | Toworakajohnkun, N.; Sukwattanasinitt, M.; Rashatasakhon, P. Tetrahedron Lett. 2017, 58, 4149. |
| [114] | Deng, T.; Yan, W.; Liu, X.; Hu, G.; Xiao, W.; Mao, S.; Lin, J.; Jiao, Y.; Jin, Y. Org. Lett. 2022, 24, 1502. |
| [115] | Nishida, K.; Ono, K.; Kato, S.; Kitamura, C. Tetrahedron Lett. 2020, 61, 152422. |
| [116] | Yang, J.-S.; Lee, Y.-R.; Yan, J.-L.; Lu, M.-C. Org. Lett. 2006, 8, 5813. |
| [117] | Jiang, H.-F.; Shen, Y.-X.; Wang, Z.-Y. Tetrahedron Lett. 2007, 48, 7542. |
| [118] | Tamaso, K.; Hatamoto, Y.; Sakaguchi, S.; Obora, Y.; Ishii, Y. J. Org. Chem. 2007, 72, 3603. |
| [119] | Piglosiewicz, I. M.; Beckhaus, R.; Saak, W.; Haase, D. J. Am. Chem. Soc. 2005, 127, 14190. |
/
| 〈 |
|
〉 |
