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Synthesis, structure and catalysis/applications of N-heterocyclic carbene based on macrocycles

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Abstract

It is well-recognized that N-heterocyclic carbenes (NHCs) ligands have provided a new dimension to the design of catalysts. Macrocyclic molecules are a class of material chemistry and have served as the synthetic hosts, and molecular recognition. In recent years, researchers have moved toward fabricating interlocking molecules with specific structures and properties. Therefore, researchers have developed more macrocycles complex based NHCs with multi-complexation modes that provide more diverse host–guest systems. In this account, this review highlights recent advances on synthesis, structure and applications of NHC based on macrocycles. According to the structure of different macrocycles, the complexes can be divided into four parts: (i) complexes of NHC based on crown ether; (ii) complexes of NHC based on porphyrin; (iii) complexes of NHC based on calixarene; (iv) complexes of NHC based on the other macrocycles. The complexes showed good coordination ability with different metal ions and showed excellent catalyst activity and optical ability.

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References

  1. Arduengo, A.J., Harlow, R.L., Kline, M.: A stable crystalline carbene. J. Am. Chem. Soc. 113, 361–363 (1991)

    Article  CAS  Google Scholar 

  2. Peris, E.: Smart N-Heterocyclic carbene ligands in catalysis. Chem. Rev. (2017). https://doi.org/10.1021/acs.chemrev.6b00695

    Google Scholar 

  3. Hahn, F.E., Jahnke, M.C.: Heterocyclic carbenes: synthesis and coordination chemistry. Angew. Chem. Int. Ed. 47, 3122–3172 (2008)

    Article  CAS  Google Scholar 

  4. Dsouza, R.N., Pischel, U., Nau, W.M.: Fluorescent dyes and their supramolecular host/guest complexes with macrocycles in aqueous solution. Chem. Rev. 111, 7941–7980 (2011)

    Article  CAS  Google Scholar 

  5. Zhang, D., Zi, G.: N-heterocyclic carbene (NHC) complexes of group 4 transition metals. Chem. Soc. Rev. 44, 1898–1921 (2015)

    Article  CAS  Google Scholar 

  6. Wegner, S., Janiak, C.: Metal nanoparticles in ionic liquids. Top. Curr. Chem. 375, 65–65 (2017)

    Article  Google Scholar 

  7. Lazreg, F., Nahra, F., Cazin, C.S.J.: Copper–NHC complexes in catalysis. Coord. Chem. Rev. 293, 48–79 (2015)

    Article  Google Scholar 

  8. Reyes, E., Uria, U., Carrillo, L., Vicario, J.: Enantioselective cascade reactions under N-Heterocyclic carbene catalysis. Synthesis 49, 451–471 (2017)

    Article  CAS  Google Scholar 

  9. Ren, Q., Li, M., Yuan, L., Wang, J.: Recent advances in N-heterocyclic carbene catalyzed achiral synthesis. Org. & Biomol. Chem. 15, 4731–4749 (2017)

    Article  CAS  Google Scholar 

  10. Nasr, A., Winkler, A., Tamm, M.: Anionic N-heterocyclic carbenes: synthesis, coordination chemistry and applications in homogeneous catalysis. Coord. Chem. Rev. 316, 68–124 (2016)

    Article  CAS  Google Scholar 

  11. Menon, R.S., Biju, A.T., Nair, V.: Recent advances in N-heterocyclic carbene (NHC)-catalysed benzoin reactions. Beil. J. Org. Chem. 12, 444–461 (2016)

    Article  CAS  Google Scholar 

  12. Matsuoka, S.I.: N-Heterocyclic carbene-catalyzed dimerization, cyclotetramerization and polymerization of Michael acceptors. Polym. J. 47, 713–718 (2015)

    Article  CAS  Google Scholar 

  13. Mahatthananchai, J., Bode, J.W.: On the mechanism of N-Heterocyclic carbene-catalyzed reactions involving acyl azoliums. Acc. Chem. Res. 47, 696–707 (2014)

    Article  CAS  Google Scholar 

  14. Hameury, S., Fremont, P., Braunstein, P.: Metal complexes with oxygen-functionalized NHC ligands: synthesis and applications. Chem. Soc. Rev. 46, 632–733 (2017)

    Article  CAS  Google Scholar 

  15. Feroci, M., Chiarotto, I., Inesi, A.: Advances in the knowledge of N-Heterocyclic carbenes properties. The backing of the electrochemical investigation. Catalysts 6, 178 (2016)

    Article  Google Scholar 

  16. Zhao, W., Ferro, V., Baker, M.V.: Carbohydrate-N-heterocyclic carbene metal complexes: synthesis, catalysis and biological studies. Coord. Chem. Rev. 339, 1–16 (2017)

    Article  CAS  Google Scholar 

  17. Hu, C., Li, X., Wang, W., Zhang, R., Ding, L.: Metal-N-Heterocyclic carbene complexes as anti-tumor agents. Curr. Med. Chem. 21, 1220–1230 (2014)

    Article  CAS  Google Scholar 

  18. Li, X., Zhou, J., Zhuo, S.: Recent progress of supported N-Heterocyclic carbene catalyst in organic reactions. Chin. J. Org. Chem. 36, 1484–1500 (2016)

    Article  CAS  Google Scholar 

  19. Ezugwu, C.I., Kabir, N.A., Yusubov, M., Verpoort, F.: Metal-organic frameworks containing N-heterocyclic carbenes and their precursors. Coord. Chem. Rev. 307, 188–210 (2016)

    Article  CAS  Google Scholar 

  20. Matsuoka, S.I.: Recent progress in N-Heterocyclic carbene chemistry: application to polymer synthesis. J. Syn. Org. Chem. Jpn. 68, 659–660 (2010)

    Article  CAS  Google Scholar 

  21. Fevre, M., Pinaud, J., Gnanou, Y., Vignolle, J., Taton, D.: N-Heterocyclic carbenes (NHCs) as organocatalysts and structural components in metal-free polymer synthesis. Chem. Soc. Rev. 42, 2142–2172 (2013)

    Article  CAS  Google Scholar 

  22. Pedersen, C.J.: Cyclic polyethers and their complexes with metal salts. J. Am. Chem. Soc. 89, 2495–2496 (1967)

    Article  CAS  Google Scholar 

  23. Li, J., Yim, D., Jang, W.D., Yoon, J.: Recent progress in the design and applications of fluorescence probes containing crown ethers. Chem. Soc. Rev. 46, 2437–2458 (2017)

    Article  CAS  Google Scholar 

  24. Powell, J., Kuksis, A., May, C.J., Nyburg, S.C., Smith, S.J.: Chelating phosphinite complexes of group 6 metal carbonyls with crown-ether-type characteristics. Effect of preferential cation binding on the reactivity of coordinated carbon monoxide. J. Am. Chem. Soc. 103, 5941–5943 (1981)

    Article  CAS  Google Scholar 

  25. Powell, J., Gregg, M., Kukiss, A., Meindl, P.: Phosphorus donor-crown ether hybrid ligands as a route to CO activation: phosphorus substituent effects and the importance of strong cation binding. J. Am. Chem. Soc. 105, 1064–1065 (1982)

    Article  Google Scholar 

  26. Powell, J., Gregg, M.R., Meindl, P.E.: Synthesis of group 6 metalla-(Aza)-crown ether tetracarbonyl influence Li+, Mg2+, and AI3+ cations on the susceptibility of the carbonyl ligand to nucleophilic addition of alkyvaryl carbanions and hydride complexes with potentially anionic amido groups. Organometallics 8, 2942–2947 (1989)

    Article  CAS  Google Scholar 

  27. Lin, I.J.B.: Synthesis, structure, and spectroscopic properties of Gold(I)—carbene complexes. Organometallics 18, 1216–1223 (1999)

    Article  Google Scholar 

  28. Hariharasarma, M., Watkins, C.L., Gray, G.M.: Solution conformational features of the unsymmetrical metalla crown ether cis-Mo(CO) 4 {2-(2,2′-O2C12H8)PO(CH2CH2O)2 -2-C20H12-2′-OP(2,2′-O2C12H8)} from 2D NMR spectroscopy and molecular modeling. Organometallics 19, 1232–1238 (2000)

    Article  CAS  Google Scholar 

  29. Duffey, C.H., Lake, C.H., Gray, G.M.: Conformationally restrained octahedral metallacrown ethers with 1,2-(Ph2P(CH2CH2O)2)2C6H4 ligands. Organometallics 17, 3550–3556 (1998)

    Article  CAS  Google Scholar 

  30. Butler, J.M., Jablonsky, M.J., Gray, G.M.: Synthesis, NMR characterization, and cation binding of metallacrown ethers with asymmetric Bis(phosphinite) and Bis(phosphite) ligands derived from 2-Hydroxy-2′-(1,4,7-trisoxo-9-nonanol)-1,1′-biphenyl. Organometallics 22, 1081–1088 (2003)

    Article  CAS  Google Scholar 

  31. Wang, J.-W., Li, Q.S., Xu, F.B., Song, H.B., Zhang, Z.Z.: Synthetic and structural studies of silver(I)- and Gold(I)-containing N-Heterocyclic carbene metallacrown ethers. Eur. Org. Chem. 2006, 1310–1316 (2006)

    Article  Google Scholar 

  32. Shrestha, S., Gimbert-Suriñach, C., Bhadbhade, M., Colbran, S.B.: Four soft donors and a hard centre: rhodium complexes of a novel tetrakis(NHC)-encapsulated crown ether ligand. Eur. Inorg. Chem. 28, 4331–4337 (2011)

    Article  Google Scholar 

  33. Shrestha, S., Mohan, B., Carolina, G.S., Colbran, S.B.: A dimer of bis-(N-heterocyclic carbene)rhodium(I) centres spanned by a dibenzo-18-crown-6 bridge from synchrotron radiation. Acta Cryst. 69, 47–48 (2013)

    Google Scholar 

  34. Wang, Y., Niu, J., Jiang, L., Niu, Y., Zhang, L.: Benzo-12-crown-4 modified N-heterocyclic carbene for organocatalyst: synthesis, characterization and degradation of block copolymers of ϵ-caprolactone withL-lactide. J. Macromol. Sci. A 53, 374–381 (2016)

    Article  CAS  Google Scholar 

  35. Nielsen, D.J., Cavell, K.J., Skelton, B.W., White, A.H.: Tetrafluoroborate anion B-F bond activation-unusual formation of a nucleophilic heterocyclic carbene: BF3 adduct. Inorg. Chim. Acta 352, 143–150 (2003)

    Article  CAS  Google Scholar 

  36. Nielsen, D.J., Cavell, K.J., Skelton, B.W., White, A.H.: Silver(I) and palladium(II) complexes of an ether-functionalized quasi-pincer bis-carbene ligand and its alkyl analogue. Organometallics 25, 4850–4856 (2006)

    Article  CAS  Google Scholar 

  37. Wang, J.-W., Song, H.B., Li, Q.S., Xu, F.B., Zhang, Z.Z.: Macrocyclic dinuclear gold(I) and silver(I) NHCs complexes. Inorg. Chim. Acta 358, 3653–3658 (2005)

    Article  CAS  Google Scholar 

  38. Holbrey, J.D., Visser, A.E., Spear, S.K., Reichert, W.M., Swatloski, R.P.: Mercury(ii) partitioning from aqueous solutions with a new, hydrophobic ethylene-glycol functionalized bis-imidazolium ionic liquid this work was presented at the green solvents for catalysis meeting held in bruchsal. Green Chem. 5, 129–135 (2003)

    Article  CAS  Google Scholar 

  39. Liu, Q.-X., Zhao, X.J., Wu, X.M., Guo, J.H., Wang, X.G.: New mercury(II) and silver(I) complexes containing NHC metallacrown ethers with the π–π stacking interactions. J. Org. Chem. 692, 5671–5679 (2007)

    Article  CAS  Google Scholar 

  40. Liu, Q.-X., Wei, Q., Liu, R., Zhao, X.J., Zhao, Z.X.: NHC macrometallocycles of mercury(ii) and silver(i): synthesis, structural studies and recognition of Hg(ii) complex 4 for silver ion. RSC Adv. 5, 28435–28447 (2015)

    Article  CAS  Google Scholar 

  41. Liu, Q.-X., Zhao, Z.X., Zhao, X.J., Wei, Q., Chen, A.H.: Structures of NHC Hg(II) and Ag(I) complexes and selective recognition of nitrate anion. Crystengcomm 17, 1358–1373 (2015)

    Article  CAS  Google Scholar 

  42. Liu, Q.-X., Chen, J.R., Sun, X.F., Zhao, X.J., Zhao, Z.X.: An NHC silver(I) macrometallocycle: synthesis, structure and selective recognition of iodide anions. Rsc. Adv. 6, 12256–12262 (2016)

    Article  CAS  Google Scholar 

  43. Wan, X.-J., Xu, F.B., Li, Q.S., Song, H.B., Zhang, Z.Z.: Synthesis and crystal structure of metal (M = Ag, Cu) crown ether with N-heterocyclic carbene linkage. Inorg. Chem. Commun. 8, 1053–1055 (2005)

    Article  CAS  Google Scholar 

  44. Wan, X.J., Xu, F.B., Zhang, Z.Z., Song, H.B.: Synthesis and crystal structure of mercury(II) metal crown ether with N-Heterocyclic carbene linkage. Z. Anorg. Allg. Chem. 635, 2381–2384 (2009)

    Google Scholar 

  45. Zhang, X., Qiu, Y., Rao, B., Luo, M.: Palladium(II)-N-heterocyclic carbene metallacrown ether complexes: synthesis, structure, and catalytic activity in the Suzuki–Miyaura reaction. Organometallics 28, 3093–3099 (2009)

    Article  CAS  Google Scholar 

  46. Zhang, W., Zhang, X., Luo, M.: Acyclic palladium(II)-N-heterocyclic carbene metallacrown ether complexes: synthesis, structure and catalytic activity. Chin. J. Chem. 30, 1423–1428 (2012)

    Article  CAS  Google Scholar 

  47. Szyszko, B., Latos-Grazynski, L.: Core chemistry and skeletal rearrangements of porphyrinoids and metalloporphyrinoids. Chem. Soc. Rev. 44, 3588–3616 (2015)

    Article  CAS  Google Scholar 

  48. Nejad, E.H., Paoniasari, A., Koning, C.E., Duchateau, R.: Semi-aromatic polyesters by alternating ring-opening copolymerisation of styrene oxide and anhydrides. Polym. Chem. 3, 1308–1313 (2012)

    Article  Google Scholar 

  49. Cao, J., Hu, D.C., Liu, J.C., Li, R.Z., Jin, N.Z.: Two self-assembled N-heterocyclic-substituted zinc porphyrins and isonicotinic acid dyads and their applications in supramolecular solar cells. Inorg. Chim. Acta 410, 126–130 (2014)

    Article  CAS  Google Scholar 

  50. Liu, X., Sternberg, E., Dolphin, D.: Cross-metathesis reactions of vinyl-chlorins and -porphyrins catalyzed by a “second generation” Grubbs’ catalyst. Chem. Commun. 7, 852–853 (2004)

    Article  Google Scholar 

  51. Richeter, S., Hadj-Aïssa, A., Taffin, C., Van, L.A., Leclercq, D.: Synthesis and structural characterisation of the first N-heterocyclic carbene ligand fused to a porphyrin. Chem. Commun. 21, 2148–2150 (2007)

    Article  Google Scholar 

  52. Abdelhameed, M., Karsenti, P.L., Langlois, A., Lefebvre, J.F., Richeter, S.: Unexpected drastic decrease in the excited-state electronic communication between porphyrin chromophores covalently linked by a palladium(II) bridge. Chem. Eur. J. 20, 12988–13001 (2014)

    Article  CAS  Google Scholar 

  53. Lefebvre, J.F., Mamadou, L., Dominique, L., Sébastien: R.: N-heterocyclic carbene (NHC) ligands annulated to free-base porphyrins: modulation of the electronic properties of the NHC upon protonation or metallation of the porphyrin. Chem. Commun. 47, 2976–2978 (2011)

    Article  CAS  Google Scholar 

  54. Lefebvre, J.F., Lo, M., Gisselbrecht, J.P., Coulembier, O., Clément, S., Richeter, S.: Porphyrins fused to N-heterocyclic carbenes (NHCs): modulation of the electronic and catalytic properties of NHCs by the central metal of the porphyrin. Chem 19, 15652–15660 (2013)

    Article  CAS  Google Scholar 

  55. Lefebvre, J.-F., Longevial, J.F., Molvinger, K., Clément, S., Richeter, S.: Porphyrins fused to N-heterocyclic carbene palladium complexes as tunable precatalysts in Mizoroki–Heck reactions: How the porphyrin can modulate the apparent catalytic activity? C. R. Chim. 19, 94–102 (2016)

    Article  CAS  Google Scholar 

  56. Longevial, J.-F., Langlois, A., Buisson, A., Devillers, C.H., Clément, S., Lee, A., harvey, P.D., Richeter, S.: Synthesis, characterization, and electronic properties of porphyrins conjugated with N-Heterocyclic carbene (NHC)–gold(I) complexes. Organometallics 35, 663–672 (2016)

    Article  CAS  Google Scholar 

  57. Wang, J.W., Meng, F.H., Zhang, L.F.: Suzuki coupling reaction of aryl halides catalyzed by an N-Heterocyclic carbene-PdCl2 species based on a porphyrin at room temperature. Organometallics 28, 2334–2337 (2009)

    Article  CAS  Google Scholar 

  58. Haumesser, J., Gisselbrecht, J.P., Karmazin-Brelot, L., Bailly, C., Weiss, J., Ruppert, R.: Synthesis and electrochemical studies of porphyrin dimers linked by metallocarbenes. Organometallics 33, 4923–4930 (2014)

    Article  CAS  Google Scholar 

  59. Xu, Y., Zhang, H., Wang, X., Liu, G.: Synthesis and catalytic study of ruthenium carbene catalyst containing a Zn-Porphyrin ligand. Chin. J. Chem. 33, 1393–1397 (2015)

    Article  CAS  Google Scholar 

  60. Toganoh, M., Hihara, T., Furuta, H.: N-heterocyclic carbene embedded in an N-confused porphyrin framework. Inorg. Chem. 49, 8182–8184 (2010)

    Article  CAS  Google Scholar 

  61. Albrecht, M., Maji, P., Häusl, C., Monney, A., Müller-Bunz, H.: N-Heterocyclic carbene bonding to cobalt porphyrin complexes. Inorg. Chim. Acta 380, 90–95 (2012)

    Article  CAS  Google Scholar 

  62. Olguin, J., Muller-Bunz, H., Albrecht, M.: Springloaded porphyrin NHC hybrid rhodium(III) complexes: carbene dissociation and oxidation catalysis. Chem. Commun. 50, 3488–3490 (2014)

    Article  CAS  Google Scholar 

  63. Anding, B.J., Ellern, A., Woo, L.K.: Comparative Study of rhodium and iridium porphyrin diaminocarbene and N-Heterocyclic carbene complexes. Organometallics 33, 2219–2229 (2014)

    Article  CAS  Google Scholar 

  64. Chan, K.H., Guan, X., Lo, K.Y., Che, M.: Elevated catalytic activity of ruthenium(II)-porphyrin-catalyzed carbene/nitrene transfer and insertion reactions with N-heterocyclic carbene ligands. Ang. Chem. Int. Ed. Engl. 53, 2982–2987 (2014)

    Article  CAS  Google Scholar 

  65. Dospil, G., Schatz, J.: Synthesis and characterization of imidazole-substituted calix[4]arenes as simple enzyme-mimics with acyltransferase activity. Tetrahedron Lett. 42, 7837–7840 (2001)

    Article  CAS  Google Scholar 

  66. Frank, M., Maas, G., Schatz, J.: Calix[4]arene-supported N-Heterocyclic carbene ligands as catalysts for suzuki cross-coupling reactions of chlorotoluene. Eur. J. Org. Chem. 2004, 607–613 (2004)

    Article  Google Scholar 

  67. Brendgen, T., Frank, M., Schatz, J.: The suzuki coupling of aryl chlorides in aqueous media catalyzed by in situ generated calix[4]arene-based N-Heterocyclic Carbene Ligands. Eur. J. Org. Chem. 2006, 2378–2383 (2006)

    Article  Google Scholar 

  68. Fahlbusch, T., Frank, M., Maas, G., Schatz, J.: N-Heterocyclic Carbene Complexes of Mercury, Silver, Iridium, platinum, ruthenium, and palladium based on the calix[4]arene skeleton. Organometallics 28, 6183–6193 (2009)

    Article  CAS  Google Scholar 

  69. Jin, C.-M., Shreeve, J.M.: Bridged Di(alkyl- and 4,4,4-trifluorobutylimidazolium) quaternary salts based on p-pert-Butylcalix[4]arene. Inorg. Chem. 43, 7532–7538 (2004)

    Article  CAS  Google Scholar 

  70. Dinarès, I., Miguel, C.G., Bardia, M.F., Solans, X., Alcalde, E.: Imidazolium-Calix[4]arene molecular frameworks: Bis(N-heterocyclic carbenes) as bidentate ligands. Organometallics 26, 5125–5128 (2007)

    Article  Google Scholar 

  71. Atwood, J.L., Koutsantonis, G.A., Raston, C.L.: Purification of C60 and C70 by selective complexation with calixarenes. Nature 368, 229–231 (1994)

    Article  CAS  Google Scholar 

  72. Suzuki, T., Nakashima, K., Shinkai, S.: Very convenient and efficient purification method for fullerene (C60) with 5,11,17,23,29,35,41,47-Octa-tert-butylcalix(8)arene- 49,50,51,52,53,54,55,56-octol. Chem. Lett. 23, 699–702 (1994)

    Article  Google Scholar 

  73. Qin, D.B., Zeng, X.S., Li, Q.S., Xu, F.B., Song, H.B., Zhang, Z.Z.: Silver(I) N-heterocyclic carbene-bridged calix[4]arene analogues as efficient [60]fullerene receptors. Chem. Commun. 2, 147–149 (2007)

    Article  Google Scholar 

  74. Lin, C.X., Kong, X.F., Li, Q.S., Zhang, Z.Z., Yuan, Y.F., Xu, F.B.: Dinuclear Ag(i) metallamacrocycles of bis-N-heterocyclic carbenes bridged by calixarene fragments: synthesis, structure and chemosensing behavior. CrystEngComm 15, 6948 (2013)

    Article  CAS  Google Scholar 

  75. Guo, L., Song, X.Z., Lin, C.X., Li, Q.S., Liu, C., Xu, F.B.: Synthesis of multi-imidazolium salt ligands containing calixarene fragments and their N-heterocyclic carbene Ag(I) macrocyclic complexes. Poly 85, 732–739 (2015)

    Article  CAS  Google Scholar 

  76. Lin, C.-X., Guo, L., Li, Q.S., Zhang, Z.Z., Yuan, Y.F., Xu, F.B.: Mono- and dinuclear Hg(II) complexes of bis-(N-heterocyclic carbene) bridged with calixarene fragments: synthesis, structure and sensing behavior. J. Org.Chem. 749, 180–187 (2014)

    Article  CAS  Google Scholar 

  77. Brenner, E., Matt, D., Henrion, M., Teci, M., Toupet, L.: Calix[4]arenes with one and two N-linked imidazolium units as precursors of N-heterocyclic carbene complexes. Coordination chemistry and use in Suzuki–Miyaura cross-coupling. Dalton Trans. 40, 9889–9898 (2011)

    Article  CAS  Google Scholar 

  78. Ren, H., Xu, Y., Jeanneau, E., Bonnamour, I., Tu, T.: Synthesis, characterization and X-ray structures of N-heterocyclic carbene palladium complexes based on calix[4]arenes: highly efficient catalysts towards Suzuki–Miyaura cross-coupling reactions. Tetrahedron 70, 2829–2837 (2014)

    Article  CAS  Google Scholar 

  79. Bidal, Y.D., Lesieur, M., Melaimi, M., Nahra, F., Cordes, D.B.: Copper(I) complexes bearing carbenes beyond classical N-heterocyclic carbenes: synthesis and catalytic activity in “click chemistry”. Cheminform 47, 3155–3161 (2016)

    Article  Google Scholar 

  80. Díez-González, S., Escudero-Adán, E.C., Benet-Buchholz, J., Steven, E.D., Slawin, A.M., Nolan, S.P.: [(NHC)CuX] complexes: synthesis, characterization and catalytic activities in reduction reactions and Click chemistry. On the advantage of using well-defined catalytic systems. Dalton Trans. 39, 7595–7606 (2010)

    Article  Google Scholar 

  81. Díaz, V.H., Ruiz, G.Y., Vandichel, M., Madder, A., Verpoort, F.: Water-soluble NHC–Cu catalysts: applications in click chemistry, bioconjugation and mechanistic analysis. Org. Bio. Chem. 12, 9350 (2014)

    Article  Google Scholar 

  82. Gaulier, C., Hospital, A., Legeret, B., Delmas, A.F., Aucagen, V., Cisnetti, F., Gautier, A.: A water soluble Cu I-NHC for CuAAC ligation of unprotected peptides under open air conditions. Chem. Commun. 43, 4005 (2012)

    Article  Google Scholar 

  83. Ourri, B., Tillement, O., Tu, T., Jeanneau, E., Darbost, U., Bonnamour, I.: Copper complexes bearing an NHC–calixarene unit: synthesis and application in click chemistry. New J. Chem. 40, 9477–9485 (2016)

    Article  CAS  Google Scholar 

  84. Patchett, R., Chaplin, A.B.: Coordination chemistry of a calix[4]arene-based NHC ligand: dinuclear complexes and comparison to I(i)Pr2Me2. Dalton Trans. 45, 8945–8955 (2016)

    Article  CAS  Google Scholar 

  85. Cram, D., Cavitands, J.: Organic hosts with enforced cavities. Science 219, 1177 (1983)

    Article  CAS  Google Scholar 

  86. Armspach, D., Bagatin, I., Engeldinger, E., Jeunesse, C., Harrowfield, J., Lejeune, M., Matt, D.: Conical cavitands as second coordination spheres and protecting environments. Toward metal-centered, intracavity reactions. J. Iran. Chem. Soc. 1, 10–19 (2004)

    Article  CAS  Google Scholar 

  87. El Moll, H., Sémeril, D., Matt, D., Toupet, L., Harrowfield, J.J.: Resorcin[4]arene-derived mono-, bis- and tetra-imidazolium salts as ligand precursors for Suzuki–Miyaura cross-coupling. Org. Biomol. Chem. 10, 372–382 (2012)

    Article  Google Scholar 

  88. Sahin, N., Semeril, D., Brenner, E., Matt, D., Kaya, C.: Palladium-catalysed Suzuki–Miyaura cross-coupling with imidazolylidene ligands substituted by crowded resorcinarenyl and calixarenyl units. T. J. Chem. 39, 1171–1179 (2015)

    Article  CAS  Google Scholar 

  89. Bullough, E.K., Little, M.A., Willans, C.E.: Electrochemical synthesis of a tetradentate copper N-heterocyclic carbene Calix[4]arene and its transmetalation to palladium: activity of the palladium complex in suzuki–miyaura cross-coupling. Organometallics 32, 570–577 (2013)

    Article  CAS  Google Scholar 

  90. Legrand, F.-X., Ménand, M., Sollogoub, M., Tilloy, S., Monflier, E.: An N-heterocyclic carbene ligand based on a beta-cyclodextrin-imidazolium salt: synthesis, characterization of organometallic complexes and Suzuki coupling. New J. Chem. 35, 2061–2065 (2011)

  91. Petter, R.C., Salek, J.S., Sikorski, C.T., Kumaravel, G., Lin, F.T.: Cooperative binding by aggregated mono-6-(alkylamino)-.beta.-cyclodextrins. J. Am. Chem. Soc. 112, 3860–3868 (1990)

  92. Ogoshi, T., Kanai, S., Fujinami, S., Yamagishi, T.A., Nakamoto, Y.: Para-bridged symmetrical Pillar[5]arenes: their Lewis acid catalyzed synthesis and host–guest property. J. Am. Chem. Soc. 130, 5022–5023 (2008)

  93. Xiao, X.-D., Bai, Y.L., Liu, J.Q., Wang, J.W.: Synthesis of novel pillar 5 arene-based N-heterocyclic carbene ligands for Pd-catalysed Heck reactions. Tetrahedron Lett. 57, 3385–3388 (2016)

  94. Xiao, X.-D., Liu, J.Q., Bai, Y.L., Wang, R.H., Wang, J.W.: Pillar[5]arene-based N-heterocyclic carbene ligand for Pd-catalysed Suzuki reaction. J. Incl. Phenom. Macro. Chem. 87, 29–36 (2016)

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Correspondence to Junwen Wang.

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Yang, J., Liu, J., Wang, Y. et al. Synthesis, structure and catalysis/applications of N-heterocyclic carbene based on macrocycles. J Incl Phenom Macrocycl Chem 90, 15–37 (2018). https://doi.org/10.1007/s10847-017-0766-9

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