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

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.

___

  • 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
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones

Yeliz DEMİR, İlhami GÜLÇİN, Barış ANIL, Mehmet KOCA, Sinan BiLGiNER

Spectrophotometric and colorimetric determination of gallium (III) with p-aminohippuric acid-functionalized citrate capped gold nanoparticles

Asiye Aslıhan AVAN

Development of a functional impedimetric immunosensor for accurate detection of thyroid-stimulating hormone

Engin ASAV

Tin-sulfur based catalysts for acetylene hydrochlorination

Xiaoqiang LUO, Gang TIAN, Yunxiao FENG, Yongjun HAN, Li WANG, Songmao CHU, Yunli CAO, Kesheng CAO, Xiaoming HU, Xuejun SHI, Songtian LI, Guoxv HE, Yibo WU, Qingbin LI, Fuxiang LI

Integrated 3D-QSAR, molecular docking, and molecular dynamics simulation studies on 1,2,3-triazole based derivatives for designing new acetylcholinesterase inhibitors

Atul Kumar SINGH, Mohammed BOUACHRINE, Shashank KUMAR, Khalil EL KHATABI, Ilham AANOUZ, Reda El-MERNISSI, Mohammed Aziz AJANA, Tahar LAKHLIFI

Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones

Songül EĞLENCE BAKIR

Evaluation of the fuel cell performances of $TiO_2$ /PAN electrospun carbon-based electrodes

Sema ASLAN

The impact of alkaline earth oxides on $Bi_2O_3$ and their catalytic activities inphotodegradation of Bisphenol A

Gülin Selda POZAN SOYLU, Sevgi KEMEÇ, Ümran ÜNLÜ

Thermal stresses in SOFC stacks: the role of mismatch among thermal conductivity of adjacent components

Özgür AYDIN, Go MATSUMOTO, Yusuke SHIRATORI

Synthesis, spectroscopic, thermal, crystal structure properties, and characterization ofnew Hofmann-$T_d$-type complexes with 3-aminopyridine

Zeki KARTAL, Onur ŞAHİN