Synthesis, characterization and catalytic properties of cationic N-heterocyclic carbene silver complexes

Three new dibenzimidazolium salts bridged by 2-methylenepropane-1,3-diyl group were synthesized. Their dinuclear N-heterocyclic carbene Ag(I) complexes were prepared by the reactions of these salts with $Ag_2 O$. The structures of the synthesized compounds were defined by nuclear magnetic resonance (NMR), Fourier-transform infrared spectroscopy (FT-IR), elemental analysis, and LC-MSMS (for complexes) techniques. Stability of the silver complexes was confirmed by 1 H NMR spectroscopy. Catalytic activities of Ag(I) compounds were tested for three-component coupling reaction of some aldehydes, amines, and phenylacetylene.

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1. Jakob CHG, Dominelli B, Rieb J, Jandl C, Pothig A et al. Dinuclear gold(I) complexes bearing N,N’-allyl-bridged bisimidazolylidene ligands. Chemistry-An Asian Journal 2020; 15 (12): 1848-1851. doi.org/10.1002/asia.202000453
2. Cervantes-Reyes A, Rominger F, Hashmi ASK. Sterically demanding Ag-I and Cu-I N-heterocyclic carbene complexes: synthesis, structures, steric parameters, and catalytic activity. Chemistry-A European Journal 2020; 26 (24): 5530-5540. doi.org/10.1002/chem.202000600
3. Ren XY, Wesolek M, Bailly C, Karmazin L, Braunstein P. Silver(I) and nickel(II) complexes with oxygen- or nitrogen-functionalized NHC ditopic ligands and catalytic ethylene oligomerization. European Journal of Inorganic Chemistry 2020; 2020 (11-12): 1073-1087. doi. org/10.1002/ejic.201901064
4. Thapa R, Kilyanek SM. Synthesis and structural characterization of 20-membered macrocyclic rings bearing trans-chelating bis(Nheterocyclic carbene) ligands and the catalytic activity of their palladium(ii) complexes. Dalton Transactions 2019; 48 (33): 12577-12590. doi.org/10.1039/C9DT02147G
5. Achar G, Shahini CR, Patil SA, Malecki JG, Budagumpi S. Coumarin-substituted 1,2,4-triazole-derived silver(I) and gold(I) complexes: synthesis, characterization and anticancer studied. New Journal of Chemistry 2019; 43 (3): 1216-1229. doi.org/10.1039/C8NJ02927J
6. Asay M, Quezada-Miriel M, Ochoa-Sanfelice JR, Martinez-Otero D. 2,6-Lutidine-linked bis-saturated NHC pincer ligands, silver complexes and transmetallation. Journal of Organometallic Chemistry 2018; 859: 10-17. doi.org/10.1016/j.jorganchem.2018.01.044
7. Chardon E, Dahm G, Guichard G, Bellemin-Laponnaz S. Synthesis and structural characterization of alkyne-functionalized N-heterocyclic carbene complexes of ruthenium, palladium and rhodium. Inorganica Chimica Acta 2017; 467: 33-38. doi.org/10.1016/j.ica.2017.07.034
8. Chen C, Zhou LQ, Xie BB, Wang YC, Ren LL, Chen XN, Cen BN, Lv H, Wang HX. Novel fast-acting pyrazole/pyridine-functionalized N-heterocyclic carbene silver complexes assembled with nanoparticles show enhanced safety and efficacy as anticancer therapeutics. Dalton Transactions 2020; 49 (8): 2505-2516. doi.org/10.1039/C9DT04751D
9. Atif M, Bhatti HN, Haque RA, Iqbal MA, Khadeer MBA, Majid AMSA. Synthesis, structure, and anticancer activity of symmetrical and non-symmetrical silver(I)-N-heterocyclic carbene complexes. Applied Biochemistry and Biotechnology 2020; 191 (3): 1171-1189. doi. org/10.1007/s12010-019-03186-9
10. Achar G, Hokrani PP, Brinda KN, Malecki JG, Budagumpi S. Synthesis, characterization, crystal structure and antibacterial properties of N- and O-functionalized (benz)imidazolium salts and their N-heterocyclic carbene silver(I) complexes. Journal of Molecular Structure 2019; 1196: 627-636. doi.org/10.1016/j.molstruc.2019.06.102
11. Holmes J, Kearsey RJ, Paske KA, Singer FN, Atallah S, Pask CM, Phillips RM, Willians CE. Tethered N-heterocyclic carbene-carboranyl silver complexes for cancer therapy. Organometallics 2019; 38 (12): 2530-2538. doi.org/10.1021/acs.organomet.9b00228
12. Loh YL, Haziz UFM, Haque RA, Amirul AA, Aidda ON, Razali MR. The effect of short alkane bridges in stability of bisbenzimidazole-2- ylidene silver(I) complexes: synthesis, crystal structure and antibacterial activity. Journal of Coordination Chemistry 2019; 72 (5-7): 894-907. doi.org/10.1080/00958972.2019.1599109
13. Fabbrini MG, Cirri D, Pratesi A, Ciofi L, Marzo T et al. A fluorescent silver(I) carbene complex with anticancer properties: Synthesis, characterization and biological studies. ChemMedChem 2019; 14 (1): 182-188. doi.org/10.1002/cmdc.201800672
14. Chotard F, Romanov AS, Hughes DL, Linnolahti M, Bochmann M. Zwitterionic mixed-carbene coinage metal complexes: synthesis, structures, and photophysical studies. European Journal of Inorganic Chemistry 2019; 2019 (39-40): 4234-4240. doi.org/10.1002/ejic.201900573
15. Atli DD, Gulle S. Dinuclear N-heterocyclic carbene silver complexes: synthesis, luminescence and catalytic studies. Journal of Molecular Structure 2019; 1179: 576-580. doi.org/10.1016/j.molstruc.2018.11.053
16. Prabusankar G, Muthukumaran N, Vaddamanu M, Raju G, Velappan K et al. Blue-emitting acridine-tagged silver(i)-bis-N-heterocyclic carbene. RSC Advances 2019; 9 (13): 7543-7550. doi.org/10.1039/C9RA00281B
17. Lin CX, Kong XF, Xu FB, Zhang ZZ, Yuan YF. Dinuclear macrocyclic quinoline bridged mercury and silver bis(N-heterocyclic carbene) complexes: Synthesis, structure, and spectroscopic studies. Zeitschrift für Anorganische und Allgemeine Chemie 2013; 639 (6): 881-885. doi. org/10.1002/zaac.201300067
18. Qin L, Ji YY, Ding T, Liu B, Wang R, Ji LZ, Gao GH. Poly(ionic liquid)s-supported N-heterocyclic carbene silver complexes for the cycloaddition of CO2 with epoxides. Catalysis Letters 2020; 150: 1196-1203. doi.org/10.1007/s10562-019-03035-8
19. Tasci Z, Kunduracioglu A, Kani I, Cetinkaya B. A new application area for Ag‐NHCs: CO2 fixation catalyst. ChemCatChem 2012; 4 (6): 831- 835. doi.org/10.1002/cctc.201100430
20. Zhang ZQ, Gao H, Wu HP, Qian YW, Chen LM et al. Chemical fixation of CO2 by using carbon material-grafted N-heterocyclic carbene silver and copper complexes. ACS Applied Nano Materials 2018; 1 (11): 6463-6476. doi.org/10.1021/acsanm.8b01679
21. Neshat A, Afrasi M, Gilanchi S, Gholinejad M. An efficient A(3) coupling catalyst based on a silver complex bearing N-heterocyclic carbene and homoscorpionate bis(3-methyl-mercaptoimidazolyl)borate ligands. ChemistrySelect 2019; 4 (32): 9268-9273. doi.org/10.1002/ slct.201901946
22. Cao J, Xu G, Li PY, Tao ML, Zhang WQ. Polyacrylonitrile fiber supported N-heterocyclic carbene Ag(I) as efficient catalysts for threecomponent coupling and intramolecular 1,3-dipolar cycloaddition reactions under flow conditions. ACS Sustainable Chemistry&Engineering 2017; 5 (4): 3438-3447. doi.org/10.1021/acssuschemeng.7b00103
23. Kilincarslan R, Sadic N. Catalytic activity of N-heterocyclic carbene silver complexes derived from imidazole ligands. Inorganic and NanoMetal Chemistry 2017; 47 (3): 462-466. doi.org/10.1080/15533174.2016.1186054
24. Li Q, Sun BC, Song HB, Tang LF. Synthesis and catalytic activity of ferrocenyl-substituted N-heterocyclic carbene silver complexes. Chemical Journal of Chinese Universities 2013; 34 (11): 2511-2516. doi.org/10.7503/cjcu20130254
25. Cheng CH, Chen DF, Song HB, Tang LF. Synthesis and catalytic activity of N-heterocyclic carbene silver complexes derived from 1-[2-(pyrazol1-yl)phenyl]imidazole. Journal of Organometallic Chemistry 2013; 726: 1-8. doi.org/10.1016/j.jorganchem.2012.12.008
26. He Y, Lv MF, Cai C. A simple procedure for polymer-supported N-heterocyclic carbene silver complex via click chemistry: an efficient and recyclable catalyst for the one-pot synthesis of propargylamines. Dalton Transactions 2012; 41 (40): 12428-12433. doi.org/10.1039/ C2DT31609A
27. Li PH, Wang L, Zhang YC, Wang M. Highly efficient three-component (aldehyde-alkyne-amine) coupling reactions catalyzed by a reusable PS-supported NHC-Ag(I) under solvent-free reaction conditions. Tetrahedron Letters 2008; 49 (47): 6650-6654. doi.org/10.1016/j. tetlet.2008.09.026
28. Abbiati G, Rossi E. Silver and gold-catalyzed multicomponent reactions. Beilstein Journal of Organic Chemistry 2014; 10: 481-513. https:// doi.org/10.3762/bjoc.10.46
29. Beillard A, Metro TX, Bantreil X, Martinez J, Lamaty F. A3-coupling reaction and [Ag(IPr)2]PF6: A successful couple. European Journal of Organic Chemistry 2017; 2107(31): 4642-4647. https://doi.org/10.1002/ejoc.201700985
30. Mariconda A, Sirignano M, Costabile C, Longo P. New NHC- silver and gold complexes active in A3-coupling (aldehyde-alkyne-amine) reaction. Molecular Catalysis 2020; 480: 110570. https://doi.org/10.1016/j.mcat.2019.110570
31. Li Y, Chen X, Song Y, Fang L, Zou G. Well-defined N-heterocyclic carbene silver halides of 1-cyclohexyl-3-arylmethylimidazolylidenes: synthesis, structure and catalysis in A3-reaction of aldehydes, amines and alkynes. Dalton Transactions 2011; 40: 2046-2052. https://doi. org/10.1039/C0DT01074J
32. Chen MT, Landers B, Navarro O. Well-defined (N-heterocyclic carbene)-Ag(I) complexes as catalysts for A3 reactions. Organic & Biomolecular Chemistry 2012; 10 (11): 2206-2208. https://doi.org/10.1039/c2ob06900h
33. Balcan S, Balcan M, Cetinkaya B. Poly(L-lactide) initiated by silver N-heterocyclic carbene complexes: synthesis, characterization and properties. Polymer Bulletin 2013; 70: 3475-3485. doi.org/10.1007/s00289-013-1034-9
34. Samantaray MK, Katiyar V, Roy D, Pang KL, Nanavati H et al. A cationic (N-heterocyclic carbene)silver complex as catalyst for bulk ring-opening polymerization of (L)-lactides. European Journal of Inorganic Chemistry 2006; 2006 (15): 2975-2984. doi.org/10.1002/ ejic.200600209
35. Thirukovela NS, Balaboina R, Kankala S, Vadde R, Vasam CS. Activation of nitriles by silver(I) N-heterocyclic carbenes: An efficient onwater synthesis of primary amides. Tetrahedron 2019; 75 (18): 2637-2641. doi.org/10.1016/j.tet.2019.03.017
36. Yoshida H, Kageyuki I, Takaki K. Silver-catalyzed highly regioselective formal hydroboration of alkynes. Organic Letters 2014; 16 (13): 3512-3515. doi.org/10.1021/ol501465x
37. Habib A, Iqbal MA, Bhatti HN. Polynuclear Ag(I)-N-heterocyclic carbene complexes: synthesis, electrochemical and in vitro anticancer study against human breast cancer and colon cancer. Journal of Coordination Chemistry 2019; 72 (12): 2065-2079. doi.org/10.1080/0095 8972.2019.1632837
38. Haziz UFM, Haque RA, Amirul AA, Shaheeda N, Razali MR. Synthesis, structures and antibacterial studies of non-functionalized and nitrile-functionalized bis-benzimidazolium salts and respective dinuclear silver(I)-N-heterocyclic carbene complexes. Polyhedron 2016; 117: 628-636. https://doi.org/10.1016/j.poly.2016.07.005
39. Haziz UFM, Haque RA, Amirul AA, Noor Aidda O, Razali MR. New class of non-symmetrical homo-dibenzimidazolium salts and their dinuclear Silver(I) di-NHC complexes. Journal of Organometallic Chemistry 2019; 899: 120914. https://doi.org/10.1016/j. jorganchem.2019.120914
40. Liu QX, Shi MC, Wang ZQ, Liu SW, Ge SS et al. 1D coordination polymers of silver(I) and copper(II) based on bis(N-heterocyclic carbene) ligands: Synthesis and structural studies. Polyhedron 2010; 29 (10): 2121-2126. doi.org/10.1016/j.poly.2010.03.025
41. Chen W, Wu B, Matsumoto K. Synthesis and crystal structure of N-heterocyclic carbene complex of silver. Journal of Organometallic Chemistry 2002; 654(1-2): 233-236. https://doi.org/10.1016/S0022-328X(02)01411-0
42. Tulloch AAD, Danopoulos AA, Winston S, Kleinhenz S, Eastham G. N-functionalised heterocyclic carbene complexes of silver. Journal of Chemical Society, Dalton Transactions 2000; 4499-4506. https://doi.org/10.1039/B007504N
43. Charra V, Tremont P, Breuil PAR, Olivier-Bourbigou H, Braunstein P. Silver(I) and copper(I) complexes with bis-NHC ligands: Dinuclear complexes, cubanes and coordination polymers. Journal of Organometallic Chemistry 2015; 795: 25-33. https://doi.org/10.1016/j. jorganchem.2015.01.025
44. Wanniarachchi YA, Khan MA, Slaughter LM. An unusually static, sterically hindered silver bis(N-heterocyclic carbene) complex and its use in transmetalation. Organometallics 2004; 23 (25): 5881-5884. https://doi.org/10.1021/om0493098
45. Dou MY, Huang XQ, Yang GY. Two inorganic-organic hybrid silver-polyoxometalates as reusable catalysts for one-pot synthesis of propargylamines via a three-component coupling reaction at room temperature. CrystEngcomm 2020; 22 (15): 2642-2648. doi. org/10.1039/D0CE00042F
46. Saadati F, Gholinejad M, Janmohammadi H, Shaybanizadeh S. Efficient method for the synthesis of propargylamines using a biomaterial containing copper nanoparticles as impressive and reusable nanocatalyst. Letters in Organic Chemistry 2018; 15 (2): 79-86. doi.org/10.21 74/1570178614666170907144234
47. Gholinejad M, Zareh F, Najera C. Iron oxide modified with pyridyl-triazole ligand for stabilization of gold nanoparticles: An efficient heterogeneous catalyst for A(3) coupling reaction in water. Applied Organometallic Chemistry 2018; 32 (9): e4454. doi.org/10.1002/ aoc.4454
48. Shah AP, Sharma AS, Jain S, Shimpi NG. Microwave assisted one pot three component synthesis of propargylamine, tetra substituted propargylamine and pyrrolo[1,2-a]quinolines using CuNPs@ZnO-PTh as a heterogeneous catalyst. New Journal of Chemistry 2018; 42 (11): 8724-8737. doi.org/10.1039/C8NJ00410B
49. Hajipour AR, Khorsandi Z, Mohammadi B. Cobalt-catalyzed three-component synthesis of propargylamine derivatives and sonogashira reaction: A comparative study between Co-NPs and Co-NHC@MWCNTs. ChemistrySelect 2019; 4 (15): 4598-4603. doi.org/10.1002/ slct.201803586
50. Slimani I, Chakchouk-Mtibaa A, Mellouli L, Mansour L, Ozdemir I, Gurbuz N, Hamdi N. Novel N-heterocyclic carbene silver(I) Complexes: Synthesis, structural characterization, antimicrobial and cytotoxicity potential studies. Journal of the Brazilian Chemical Society 2020; 31 (10): 2058-2070. https://doi.org/10.21577/0103-5053.20200107
51. Gurbuz N, Yasar S, Ozcan EO, Ozdemir I, Cetinkaya B. Transfer hydrogenation of ketones by ruthenium complexes bearing benzimidazol2-ylidene ligands. European Journal of Inorganic Chemistry 2010; 2010 (19): 3051-3056. https://doi.org/10.1002/ejic.201000181,
52. Han Y, Tian Z, Zhang S, Liu X, Li J. Half-sandwich iridiumIII N-heterocyclic carbene antitumor complexes and biological applications. Journal of Inorganic Biochemistry 2018; 189: 163-171. doi.org/10.1016/j.jinorgbio.2018.09.009
53. Liu Q, Wu H, Zhao Z, Wei D. Macrometallocycle binuclear NHC silver(I) complex with bridging azobenzene: synthesis, structure and recognition for hydrogen sulfate. Tetrahedron 2019; 75 (23): 3128-3134. doi.org/10.1016/j.tet.2019.04.066
54. Demir Atli D. Synthesis and catalytic application of cyclopentadienyl nickel(II) N-heterocyclic carbene complexes. Journal of Coordination Chemistry 2020; 73 (10): 1530-1537. doi.org/10.1080/00958972.2020.1786543
55. Kilincarslan R, Sadic N, Cetinkaya B. Ag(I) complexes of benzimidazol-2-ylidene ligands: a study of catalytic efficiency towards threecomponent coupling reactions. Turkish Journal of Chemistry 2016; 40 (4): 681-687. doi.org/10.3906/kim-1510-6
56. Peshkov V.A, Pereshivko O.P, Van der Eycken E.V. A walk around the A3-coupling. Chemical Society Reviews 41 (2012) 3790-3807. https://doi.org/10.1039/C2CS15356D.
57. Chen J.-J, Gan Z.-L, Huang Q, Yi X.-Y. Well-defined dinuclear silver phosphine complexes based on nitrogen donor ligand and their high efficient catalysis for A3-coupling reaction. Inorganica Chimica Acta 466 (2017) 93-99. https://doi.org/10.1016/j.ica.2017.05.018.
58. Esfandiary N, Pazoki F, Nakisa A, Azizi K, Radfar I et al. Silver chloride supported on Vitamin B1 –Organometallic magnetic catalyst: synthesis, density functional theory study and application in A3-coupling reactions. Applied Organometallic Chemistry 34 (2020) e5725. https://doi.org/10.1002/aoc.5725