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.
Similar content being viewed by others
References
Arduengo, A.J., Harlow, R.L., Kline, M.: A stable crystalline carbene. J. Am. Chem. Soc. 113, 361–363 (1991)
Peris, E.: Smart N-Heterocyclic carbene ligands in catalysis. Chem. Rev. (2017). https://doi.org/10.1021/acs.chemrev.6b00695
Hahn, F.E., Jahnke, M.C.: Heterocyclic carbenes: synthesis and coordination chemistry. Angew. Chem. Int. Ed. 47, 3122–3172 (2008)
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)
Zhang, D., Zi, G.: N-heterocyclic carbene (NHC) complexes of group 4 transition metals. Chem. Soc. Rev. 44, 1898–1921 (2015)
Wegner, S., Janiak, C.: Metal nanoparticles in ionic liquids. Top. Curr. Chem. 375, 65–65 (2017)
Lazreg, F., Nahra, F., Cazin, C.S.J.: Copper–NHC complexes in catalysis. Coord. Chem. Rev. 293, 48–79 (2015)
Reyes, E., Uria, U., Carrillo, L., Vicario, J.: Enantioselective cascade reactions under N-Heterocyclic carbene catalysis. Synthesis 49, 451–471 (2017)
Ren, Q., Li, M., Yuan, L., Wang, J.: Recent advances in N-heterocyclic carbene catalyzed achiral synthesis. Org. & Biomol. Chem. 15, 4731–4749 (2017)
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)
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)
Matsuoka, S.I.: N-Heterocyclic carbene-catalyzed dimerization, cyclotetramerization and polymerization of Michael acceptors. Polym. J. 47, 713–718 (2015)
Mahatthananchai, J., Bode, J.W.: On the mechanism of N-Heterocyclic carbene-catalyzed reactions involving acyl azoliums. Acc. Chem. Res. 47, 696–707 (2014)
Hameury, S., Fremont, P., Braunstein, P.: Metal complexes with oxygen-functionalized NHC ligands: synthesis and applications. Chem. Soc. Rev. 46, 632–733 (2017)
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)
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)
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)
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)
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)
Matsuoka, S.I.: Recent progress in N-Heterocyclic carbene chemistry: application to polymer synthesis. J. Syn. Org. Chem. Jpn. 68, 659–660 (2010)
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)
Pedersen, C.J.: Cyclic polyethers and their complexes with metal salts. J. Am. Chem. Soc. 89, 2495–2496 (1967)
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)
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)
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)
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)
Lin, I.J.B.: Synthesis, structure, and spectroscopic properties of Gold(I)—carbene complexes. Organometallics 18, 1216–1223 (1999)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
Szyszko, B., Latos-Grazynski, L.: Core chemistry and skeletal rearrangements of porphyrinoids and metalloporphyrinoids. Chem. Soc. Rev. 44, 3588–3616 (2015)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
Toganoh, M., Hihara, T., Furuta, H.: N-heterocyclic carbene embedded in an N-confused porphyrin framework. Inorg. Chem. 49, 8182–8184 (2010)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
Atwood, J.L., Koutsantonis, G.A., Raston, C.L.: Purification of C60 and C70 by selective complexation with calixarenes. Nature 368, 229–231 (1994)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
Cram, D., Cavitands, J.: Organic hosts with enforced cavities. Science 219, 1177 (1983)
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)
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)
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)
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)
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)
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)
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)
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)
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)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10847-017-0766-9