Citation: Veronica Iuliano, Placido Neri, Margherita De Rosa, Paolo Della Sala, Carmine Gaeta, Carmen Talotta. Indane synthesis in resorcinarene capsules: The crucial role of the carbocation counter anion[J]. Chinese Chemical Letters, ;2026, 37(10): 112261. doi: 10.1016/j.cclet.2025.112261 shu

Indane synthesis in resorcinarene capsules: The crucial role of the carbocation counter anion

Laboratory of Supramolecular Chemistry, Dipartimento di Chimica e Biologia “A. Zambelli”, Università di Salerno, Fisciano I-84084, Italy

viuliano@unisa.it

cgaeta@unisa.it

ctalotta@unisa.it

Received Date: 29 July 2025
Revised Date: 4 December 2025
Accepted Date: 9 December 2025
Available Online: 11 December 2025

Figures(4)

This study elucidates the pivotal role of hexameric capsule C in the Brønsted acid-catalyzed dimerization of styrenes to indanes. The confined environment significantly influences the reaction outcomes and requires the co-encapsulation of acid counter-anions for the effective stabilization of carbocation intermediates. These results indicate the potential to optimize the catalytic activity of hexameric capsule C through careful selection of suitable carbocation counter-anions.
- Supramolecular catalysis,
- Resorcinarene hexameric capsule,
- Confined-space chemistry,
- Counter-anion effect,
- Indane synthesis
1. [1]
  L.R. MacGillivray, J.L. Atwood, Nature 389 (1997) 469‒472. doi: 10.1038/38985
2. [2]
  L. Avram, Y. Cohen, J. Am. Chem. Soc. 124 (2002) 15148‒15149. doi: 10.1021/ja0272686
3. [3]
  Q. Zhang, L. Catti, K. Tiefenbacher, Acc. Chem. Res. 51 (2018) 2107–2114. doi: 10.1021/acs.accounts.8b00320
4. [4]
  G. Borsato, J. Rebek Jr., A. Scarso, Capsules and cavitands: synthetic catalysts of nanometric dimension, in: A. Zecchina, S. Bordiga, E.E. Groppo (Eds.), Selective Nanocatalysts and Nanoscience: Concepts for Heterogeneous and Homogeneous Catalysis, Wiley-VCH, Weinheim, 2011, pp. 105–168.
5. [5]
  C. Wang, L. Xu, Z. Jia, T.P. Loh, Chin. Chem. Lett. 35 (2024) 109075. doi: 10.1016/j.cclet.2023.109075
6. [6]
  K. Wang, Q. Liu, L. Zhou, et al., Chin. Chem. Lett. 34 (2023) 108559. doi: 10.1016/j.cclet.2023.108559
7. [7]
  V. Iuliano, P. Della Sala, C. Talotta, et al., Curr. Opin. Colloid Interface Sci. 65 (2023) 101692. doi: 10.1016/j.cocis.2023.101692
8. [8]
  P. La Manna, C. Talotta, G. Floresta, et al., Angew. Chem. Int. Ed. 57 (2018) 5423‒5428. doi: 10.1002/anie.201801642
9. [9]
  V. Iuliano, C. Talotta, M. De Rosa, et al., Org. Lett. 25 (2023) 6464–6468. doi: 10.1021/acs.orglett.3c01935
10. [10]
  S. Gambaro, C. Talotta, P.D. Sala, et al., J. Am. Chem. Soc. 142 (2020) 14914–14923. doi: 10.1021/jacs.0c04705
11. [11]
  S. Gambaro, M. De Rosa, A. Soriente, et al., Org. Chem. Front. 6 (2019) 2339–2347. doi: 10.1039/c9qo00224c
12. [12]
  Q. Zhang, J. Rinkel, B. Goldfuss, J.S. Dickschat, K. Tiefenbcher, Nat. Catal. 1 (2018) 609–615. doi: 10.1038/s41929-018-0115-4
13. [13]
  Q. Zhang, K. Tiefenbacher, Nat. Chem. 7 (2015) 197–202. doi: 10.1038/nchem.2181
14. [14]
  S. Merget, L. Catti, G. Piccini, K. Tiefenbacher, J. Am. Chem. Soc. 142 (2020) 4400–4410. doi: 10.1021/jacs.9b13239
15. [15]
  Cornu, L.D. Syntrivanis, K. Tiefenbacher, Nat. Protoc. 19 (2024) 313–339. doi: 10.1038/s41596-023-00919-3
16. [16]
  T. Zhang, V. Bandero, C. Corcoran, et al., Eur. J. Pharm. Sci. 188 (2023) 106529. doi: 10.1016/j.ejps.2023.106529
17. [17]
  L.M. Leoni, E. Hamel, D. Genini, et al., J. Natl. Cancer Inst. 92 (2000) 217–224. doi: 10.1093/jnci/92.3.217
18. [18]
  C.B. Xue, L. Chen, G. Cao, et al., ACS Med. Chem. Lett. 1 (2010) 483–487. doi: 10.1021/ml1001536
19. [19]
  G. Bartolo R. Mancuso, L. Veltri Chem. Eur. J. 22 (2016) 5056–5094. doi: 10.1002/chem.201503933
20. [20]
  P.J. Chua, B. Tan, L. Yang, et al., Chem. Commun. 46 (2010) 7611–7613. doi: 10.1039/c0cc01577f
21. [21]
  C.P. Johnston, A. Kothari, T. Sergeieva, et al., Nat. Chem. 7 (2015) 171–177. doi: 10.1038/nchem.2150
22. [22]
  M.C. Davis, A.J. Guenthner, T.J. Groshens, J.T. Reams, J.M. Mabry, J. Polym. Sci. A Polym. Chem. 50 (2012) 4127–4136. doi: 10.1002/pola.26218
23. [23]
  A.H. Farquhar, K.E. Gardner, S. Acosta-Calle, et al., Organometallics 41 (2022) 3366–3372. doi: 10.1021/acs.organomet.2c00315
24. [24]
  J.M. Begouin, F. Capitta, X. Wu, M. Niggemann, Org. Lett. 15 (2013) 1370–1373. doi: 10.1021/ol400341p
25. [25]
  S. Horiuchi, C. Matsuo, E. Sakuda, et al., Dalton Trans. 49 (2020) 8472–8477. doi: 10.1039/d0dt01485k
26. [26]
  Q. Zhang, L. Catti, V.R.I. Kaila, K. Tiefenbacher, Chem. Sci. 8 (2017) 1653–1657. doi: 10.1039/C6SC04565K
27. [27]
  M. De Rosa, S. Gambaro, A. Soriente, et al., Chem. Sci. 13 (2022) 8618–8625. doi: 10.1039/d2sc02901d
28. [28]
  H. Ichou, K. Telliez, S. Lajnef, F. Peyrot, B. Doistau, L. Leherte, B. Colasson, Inorg. Chem. Front. 12 (2025) 1028–1039. doi: 10.1039/d4qi02896a
29. [29]
  A. Shivanyuk, J. Rebek Jr, Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 7662–7665. doi: 10.1073/pnas.141226898
1. [1]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
2. [2]
  Xianchen Hu , Junli Yang , Fang Gao , Zhiyong Zhao , Simin Liu . Highly selective [4+4] cross-photodimerization of (4a-azonia)anthracenes driven by confinement of D-A hetero-guest pair in cucurbit[10]uril host. Chinese Chemical Letters, 2025, 36(3): 109967-. doi: 10.1016/j.cclet.2024.109967
3. [3]
  Jinchen Li , Tangxin Xiao , Kai Diao , Zhouyu Wang , Leyong Wang . Supramolecular catalysis enabled by chiral molecular cages with anion-π interaction capability. Chinese Chemical Letters, 2026, 37(1): 111796-. doi: 10.1016/j.cclet.2025.111796
4. [4]
  Xianya Yao , Ning Han , Hui Liu , Lingbao Xing . Construction of donor-acceptor supramolecular organic framework with enhanced superoxide anion radical generation for photocatalytic synthesis of benzimidazole. Chinese Chemical Letters, 2026, 37(5): 111426-. doi: 10.1016/j.cclet.2025.111426
5. [5]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
6. [6]
  Haitao Liu , Youlin Deng , Dan Ling , Lingzhu Chen , Zhichao Jin . Asymmetric catalysis for the synthesis of planar chiral ferrocene derivatives. Chinese Chemical Letters, 2026, 37(3): 111793-. doi: 10.1016/j.cclet.2025.111793
7. [7]
  Tianyi Zhou , Heng Yang , Guangbin Zhou , Feng Chen , Pan Gao . Recent advances of heterogeneous manganese catalysis in organic synthesis. Chinese Chemical Letters, 2026, 37(6): 112223-. doi: 10.1016/j.cclet.2025.112223
8. [8]
  Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
9. [9]
  Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896
10. [10]
  Pei Xu , Tian-Zi Hao , Zhi-Tao Liu , Yi-Qin Liu , Hui-Xian Jiang , Dong Guo , Xu Zhu . Visible-light-induced dual catalysis for divergent reduction of nitro compounds with CO₂ radical anion. Chinese Chemical Letters, 2025, 36(10): 110899-. doi: 10.1016/j.cclet.2025.110899
11. [11]
  Jing JIN , Zhuming GUO , Zhiyin XIAO , Xiujuan JIANG , Yi HE , Xiaoming LIU . Tuning the stability and cytotoxicity of fac-[Fe(CO)₃I₃]^- anion by its counter ions: From aminiums to inorganic cations. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 991-1004. doi: 10.11862/CJIC.20230458
12. [12]
  Jiajia Zhuang , Chunyu Cui , Changjiang Li , Gang Luo , Jiaping Tong , Di Sun . Counter-ion effect to the Ising-type magnetic anisotropy and magnetic relaxation in trigonal bipyramidal Co(Ⅱ) complexes. Chinese Chemical Letters, 2025, 36(7): 110091-. doi: 10.1016/j.cclet.2024.110091
13. [13]
  Ziyan Wang , Yihe Gao , Chao Han . A breakthrough approach to hydrogen peroxide synthesis: Defect-enhanced catalysis in SnSe nanosheets. Chinese Journal of Structural Chemistry, 2025, 44(10): 100679-100679. doi: 10.1016/j.cjsc.2025.100679
14. [14]
  Jun Shi , Xueting Zhou , Bing-Qing Yang , Biaobiao Jiang , Wei Wu , Hai Ren . Single-electron transfer enables enantioselective synthesis of spirooxindoles via dual copper and phosphoric acid catalysis. Chinese Chemical Letters, 2026, 37(4): 111250-. doi: 10.1016/j.cclet.2025.111250
15. [15]
  Yuqi Zhu , Suhua Chen , Jianping Zou , Bo Li , Wei Ren , Gaoxia Zhang , Jiajie Wang , Xinyu Liu , Qianhui Li , Huiying Zhang , Fanying Xia . Single-atom catalysts partner with defects to open a new chapter in catalysis: Synthesis, performances, and mechanisms. Chinese Chemical Letters, 2026, 37(7): 112192-. doi: 10.1016/j.cclet.2025.112192
16. [16]
  Yan Zong , Qiuchen Huang , Xiaomei Zou , Qifan Zhou , Yuanmei Wen , Dong Li , Yongzhi Chen , Xuefeng Tan , Gen-Qiang Chen , Xumu Zhang . Enantioselective total synthesis of 3-deoxy-epothilone B enabled by efficient asymmetric catalysis. Chinese Chemical Letters, 2026, 37(8): 112162-. doi: 10.1016/j.cclet.2025.112162
17. [17]
  Zhenzhu Wang , Chenglong Liu , Yunpeng Ge , Wencan Li , Chenyang Zhang , Bing Yang , Shizhong Mao , Zeyuan Dong . Differentiated self-assembly through orthogonal noncovalent interactions towards the synthesis of two-dimensional woven supramolecular polymers. Chinese Chemical Letters, 2024, 35(5): 109127-. doi: 10.1016/j.cclet.2023.109127
18. [18]
  Chengye Lou , Yu Hu , Yunjia Jiang , Lingyao Wang , Yuanbin Zhang . Borane cage hybrid supramolecular metal-organic frameworks (BSFs): Design, synthesis and gas separation performance. Chinese Journal of Structural Chemistry, 2026, 45(2): 100789-100789. doi: 10.1016/j.cjsc.2025.100789
19. [19]
  Wenya DING , Fangfei XU , Jiayu GU , Xinran CHEN , Kai CHEN . Synthesis and crystal structure of three cucurbit[6]uril-cadmium supramolecular assemblies. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 808-816. doi: 10.11862/CJIC.20260012
20. [20]
  Xuanyu Wang , Zhao Gao , Wei Tian . Supramolecular confinement effect enabling light-harvesting system for photocatalytic α-oxyamination reaction. Chinese Chemical Letters, 2024, 35(11): 109757-. doi: 10.1016/j.cclet.2024.109757

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(4)
HTML views(0)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142