[en] Recently, graphitic carbon nitride (g-C3N4) has attracted great attention among the most promising materials in heterogeneous catalysis. Herein, we describe an application of ammonium iodide-coated g-C3N4 (NH4I@g-C3N4) as a new and sustainable heterogeneous catalyst for the selective N1-alkylation of pyrimidines. Structural, morphological, and spectroscopic analyses of NH4I@g-C3N4 were carried out through X-ray diffraction (XRD), scanning electronic microscopy (SEM), ultra-violet visible spectroscopy (UV-visible) and Fourier-transform infrared spectroscopy (FTIR). The obtained results prove that the NH4I@g-C3N4 is well prepared. Moreover, it was applied as an efficient catalyst in the synthesis of nucleoside analogs through the N1-alkylation reaction of pyrimidine nucleobases. Several alkylating agents were tested with various parameters to achieve excellent selectivity and high yields. This novel eco-friendly catalyst showed a catalytic activity and good selectivity in the synthesis of nucleoside analogs without noticeable changes in the morphology.
Disciplines :
Chemistry
Author, co-author :
Elmoussaoui, Soukaina; Laboratory of Molecular Chemistry, Faculty of Science Semlalia, Cadi Ayyad University, Marrakesh, Morocco
Lachhab, Saida; Laboratory of Molecular Chemistry, Faculty of Science Semlalia, Cadi Ayyad University, Marrakesh, Morocco
El Mansouri, Az-Eddine; Chemistry Department, University of the Free State, Bloemfontein, South Africa
Fkhar, Lahcen ; Université de Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM)
Mehdi, Ahmad ; ICGM, Univ Montpellier, CNRS, ENSCM, Montpellier, France
Sanghvi, Yogesh S.; Rasayan Inc., Encinitas, United States
Ait-Ali, Mustapha ; Laboratory of Molecular Chemistry, Faculty of Science Semlalia, Cadi Ayyad University, Marrakesh, Morocco
Lazrek, Hassan B. ; Laboratory of Molecular Chemistry, Faculty of Science Semlalia, Cadi Ayyad University, Marrakesh, Morocco
Language :
English
Title :
A mild protocol for the development of an innovative green heterogeneous catalyst for the Hilbert-Johnson reaction
de Oliveira P. F. M. Torresi R. M. Emmerling F. Camargo P. H. C. Challenges and opportunities in the bottom-up mechanochemical synthesis of noble metal nanoparticles J. Mater. Chem. A 2020 8 32 16114 16141 https://dx.doi.org/10.1039/D0TA05183G 10.1039/D0TA05183G
Liu C. Zhang J. Wang W. Chen L. Zhu M. Progress in the synthesis and applications of N-rich carbon nitride (C3N5)-based catalysts in environmental and energy catalysis Surf. Interfaces 2023 42 103491 https://dx.doi.org/10.1016/j.surfin.2023.103491 10.1016/j.surfin.2023.103491
Zimmerman J. B. Anastas P. T. Erythropel H. C. Leitner W. Designing for a green chemistry future Sci. 2020 367 6476 397 400 https://dx.doi.org/10.1126/science.aay3060 10.1126/science.aay3060 31974246
Zhao W. Make the chemical industry clean with green chemistry: an interview with Buxing Han Natl. Sci. Rev. 2018 5 6 953 956 https://dx.doi.org/10.1093/nsr/nwy045 10.1093/nsr/nwy045
Theerthagiri J. Karuppasamy K. Park J. Rahamathulla N. Kumari M. L. A. Souza M. K. R. Cardoso E. S. F. Murthy A. P. Maia G. Kim H. S. Choi M. Y. Electrochemical conversion of biomass-derived aldehydes into fine chemicals and hydrogen: A review Environ. Chem. Letters 2023 21 3 1555 1583 https://dx.doi.org/10.1007/s10311-022-01543-5 10.1007/s10311-022-01543-5
Medjahed N. Kibou Z. Berrichi A. Choukchou-Braham N. Advances in Pyrazoles Rings’ Syntheses by Heterogeneous Catalysts, Ionic Liquids, and Multicomponent Reactions - A Review Curr. Org. Chem. 2023 27 6 471 509 https://dx.doi.org/10.2174/1385272827666230602121855 10.2174/1385272827666230602121855
Maddila S. N. Maddila S. van Zyl W. E. Jonnalagadda S. B. Mn doped ZrO2 as a green, efficient and reusable heterogeneous catalyst for the multicomponent synthesis of pyrano [2, 3-d]-pyrimidine derivatives RSC Adv. 2015 5 47 37360 37366 https://dx.doi.org/10.1039/b000000x 10.1039/C5RA06373F
Ahmed A. Iqbal M. Z. Dahshan A. Khan J. Helmy Hegazy H. Exploring the porous organic frameworks with carbonaceous materials for superior electrochemical performance of hybrid supercapacitors J. Electroanal. Chem. 2023 950 117869 https://dx.doi.org/10.1016/j.jelechem.2023.117869 10.1016/j.jelechem.2023.117869
Khandare L. N. Late D. J. Chaure N. B. Engineered two-dimensional molybdenum disulfide/carbonaceous hybrid nanostructures for supercapacitors development J. Energy Storage 2023 74 109336 https://dx.doi.org/10.1016/j.est.2023.109336 10.1016/j.est.2023.109336
Ong W. J. Tan L. L. Ng Y. H. Yong S. T. Chai S. P. Graphitic carbon nitride (g-C3N4)-based photocatalysts for artificial photosynthesis and environmental remediation: are we a step closer to achieving sustainability Chem. Rev. 2016 116 12 7159 7329 https://dx.doi.org/10.1021/acs.chemrev.6b00075 10.1021/acs.chemrev.6b00075 27199146
Dong G. Ho W. Li Y. Zhang L. Facile Synthesis of Porous Graphene-Like Carbon Nitride (C6N9H3) with Excellent Photocatalytic Activity for NO Removal Appl. Catal., B 2015 174 477 485 https://dx.doi.org/10.1016/j.apcatb.2015.03.035 10.1016/j.apcatb.2015.03.035
Fang J. Fan H. Li M. Long C. Nitrogen Self-Doped Graphitic Carbon Nitride as Efficient Visible Light Photocatalyst for Hydrogen Evolution J. Mater. Chem. A 2015 3 26 13819 13826 https://dx.doi.org/10.1039/c5ta02257f 10.1039/C5TA02257F
Shi L. Wang T. Zhang H. Chang K. Ye J. Electrostatic Self-Assembly of Nanosized Carbon Nitride Nanosheet onto a Zirconium Metal−Organic Framework for Enhanced Photocatalytic CO2 Reduction Adv. Funct. Mater. 2015 25 33 5360 5367 https://dx.doi.org/10.1002/adfm.201502253 10.1002/adfm.201502253
Schwinghammer K. Tuffy B. Mesch M. B. Wirnhier E. Martineau C. Taulelle F. Schnick W. Senker J. Lotsch B. V. Triazine-Based Carbon Nitrides for Visible-Light-Driven Hydrogen Evolution Angew. Chem., In. Ed. 2013 52 9 2435 2439 https://dx.doi.org/10.1002/anie.201206817 10.1002/anie.201206817
Liu J. Wang H. Chen Z. P. Moehwald H. Fiechter S. van de Krol R. Wen L. Jiang L. Antonietti M. Microcontact-Printing-Assisted Access of Graphitic Carbon Nitride Films with Favorable Textures toward Photoelectrochemical Application Adv. Mater. 2015 27 4 712 718 https://dx.doi.org/10.1002/adma.201404543 10.1002/adma.201404543 25492578
Zhang Z. Jiang D. Li D. He M. Chen M. Construction of SnNb2O6 Nanosheet/g-C3N4 Nanosheet Two-Dimensional Heterostructures with Improved Photocatalytic Activity: Synergistic Effect and Mechanism Insight Appl. Catal., B 2016 183 113 123 https://dx.doi.org/10.1016/j.apcatb.2015.10.022 10.1016/j.apcatb.2015.10.022
Yu J. Wang K. Xiao W. Cheng B. Photocatalytic reduction of CO 2 into hydrocarbon solar fuels over gC3N4-Pt nanocomposite photocatalysts Phys. Chem. Chem. Phys. 2014 16 23 11492 11501 https://dx.doi.org/10.1039/c4cp00133h 10.1039/C4CP00133H 24801641
Cui Y. Zhang G. Lin Z. Wang X. Condensed and LowDefected Graphitic Carbon Nitride with Enhanced Photocatalytic Hydrogen Evolution under Visible Light Irradiation Appl. Catal., B 2016 181 413 419 https://dx.doi.org/10.1016/j.apcatb.2015.08.018 10.1016/j.apcatb.2015.08.018
Ma J. Tan X. Jiang F. Yu T. Graphitic C3N4 nanosheet-sensitized brookite TiO2 to achieve photocatalytic hydrogen evolution under visible light Catal. Sci. Technol. 2017 7 15 3275 3282 10.1039/C7CY00788D
Hu X. Zhang W. Yong Y. Xu Y. Wang X. Yao X. One-step synthesis of iodine-doped g-C3N4 with enhanced photocatalytic nitrogen fixation performance Appl. Surf. Sci. 2020 510 145413 https://dx.doi.org/10.1016/j.apsusc.2020.145413 10.1016/j.apsusc.2020.145413
Elavarasan S. Baskar B. Senthil C. Bhanja P. Bhaumik A. Selvam P. Sasidharan M. An efficient mesoporous carbon nitride (g-C3N4) functionalized Pd catalyst for carbon-carbon bond formation reactions RSC Adv. 2016 6 55 49376 49386 https://dx.doi.org/10.1039/C6RA04170A 10.1039/C6RA04170A
Cai Y. L. Wang P. Zhang Y. Enhanced photocatalytic properties of s-triazine-based-g-C3N4/BlueP and g-C3N4/G/BlueP vdW heterostructures: A DFT study Chem. Phys. Lett. 2024 841 141163 https://dx.doi.org/10.1016/j.cplett.2024.141163 10.1016/j.cplett.2024.141163
Wang Y. Zhang J. Wang X. Antonietti M. Li H. Boron-and fluorine-containing mesoporous carbon nitride polymers: metal-free catalysts for cyclohexane oxidation Angew. Chem., In. Ed. 2010 19 49 3356 3359 https://dx.doi.org/10.1002/anie.201000120 10.1002/anie.201000120 20340148
Thomas A. Fischer A. Goettmann F. Antonietti M. Müller J. O. Schlögl R. Carlsson J. M. Graphitic carbon nitride materials: variation of structure and morphology and their use as metal-free catalysts J. Mater. Chem. 2008 18 41 4893 4908 https://dx.doi.org/10.1039/b800274f 10.1039/B800274F
Goettmann F. Fischer A. Antonietti M. Thomas A. Metal-free catalysis of sustainable Friedel-Crafts reactions: direct activation of benzene by carbon nitrides to avoid the use of metal chlorides and halogenated compounds Chem. Commun. 2006 4530 4532 https://dx.doi.org/10.1039/b608532f 10.1039/B608532F 17283808
Ansari M. B. Min B. H. Mo Y. H. Park S. E. CO2 activation and promotional effect in the oxidation of cyclic olefins over mesoporous carbon nitrides G. Chem. 2011 13 6 1416 1421 https://dx.doi.org/10.1039/c0gc00951b 10.1039/C0GC00951B
Xu J. Shang J. K. Jiang Q. Wang Y. Li Y. X. Facile alkali-assisted synthesis of g-C3N4 materials and their high-performance catalytic application in solvent-free cycloaddition of CO2 to epoxides RSC Adv. 2016 6 60 55382 55392 https://dx.doi.org/10.1039/C6RA10509B 10.1039/C6RA10509B
Yu X. Zhan Y. Fan T. Zhang Y. Liang S. Sun L. Hu X. Fang W. Chen Z. Yi X. Encapsulating Pd/g-C3N4 with acrylic acid to enhance the catalytic partial hydrogenation performance of isoprene Carbone 2023 201 1174 1183 https://dx.doi.org/10.1016/j.carbon.2022.10.039 10.1016/j.carbon.2022.10.039
Elavarasan S. Baskar B. Senthil C. Bhanja P. Bhaumik A. Selvam P. Sasidharan M. An efficient mesoporous carbon nitride (gC3N4) functionalized Pd catalyst for carbon-carbon bond formation reactions RSC Adv. 2016 6 55 49376 49386 https://dx.doi.org/10.1039/C6RA04170A 10.1039/C6RA04170A
Gao J. Wang Y. Zhou S. Lin W. Kong Y. A facile one-step synthesis of Fe-doped g-C3N4 nanosheets and their improved visible-light photocatalytic performance ChemCatChem 2017 9 9 1708 1715 https://dx.doi.org/10.1002/cctc.201700492 10.1002/cctc.201700492
Fard M. A. D. Ghafuri H. Rashidizadeh A. Sulfonated highly ordered mesoporous graphitic carbon nitride as a super active heterogeneous solid acid catalyst for Biginelli reaction Microporous. Mesoporous. Mater. 2019 274 83 93 https://dx.doi.org/10.1016/j.micromeso.2018.07.030 10.1016/j.micromeso.2018.07.030
Verma S. Baig R. N. Han C. Nadagouda M. N. Varma R. S. Oxidative esterification via photocatalytic C-H activation G. Chem. 2016 18 1 251 254 10.1039/C5GC02025E
Niedballa U. Vorbrueggen H. Synthesis of nucleosides 17. A general synthesis of N-glycosides. 6. On the mechanism of the stannic chloride catalyzed silyl Hilbert-Johnson reaction J. Org. Chem. 1976 41 12 2084 2086 https://dx.doi.org/10.1021/jo00874a002 10.1021/jo00874a002 932850
Vorbruggen H. Krolikiewicz K. Bennua B. Nucleoside syntheses, XXII(1) Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts Chem. Ber. 1981 114 4 1234 1255 https://dx.doi.org/10.1002/cber.19811140404 10.1002/cber.19811140404
Vorbrüggen H. Ruh-Pohlenz C. Synthesis of nucleosides Org. React. 2004 55 1 630 https://dx.doi.org/10.1002/0471264180.or055.01
Chengyuan L. Weihui J. Shunjun D. Han S. Gennian M. Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction Molecules 2017 22 1 84 https://dx.doi.org/10.3390/molecules22010084 10.3390/molecules22010084 28067759
Lazrek H. B. Baddi L. Smietana M. Vasseur J. J. Sebti S. Zahouily M. One-Pot Synthesis of Antiviral Acyclovir and Other Nucleosides Derivatives Using Doped Natural Phosphate as Lewis Acid Catalyst Nucleosides, Nucleotides Nucleic Acids 2008 27 10-11 1107 1112 https://dx.doi.org/10.1080/15257770802341285 10.1080/15257770802341285 18788041
El Mansouri Az Zahouily M. Lazrek H. B. HMDS/KI a simple, a cheap and efficient catalyst for the one-pot synthesis of N-functionalized pyrimidines Synth. Comm. 2019 49 14 1802 1812 https://dx.doi.org/10.1080/00397911.2019.1602655 10.1080/00397911.2019.1602655
Belkharchach S. Ighachane H. Lachgar A. Ait Ali M. Lazrek H. B. Efficient and selective catalytic N-Alkylation of pyrimidine by ammonium Sulfate@ Hydro-thermal carbone under eco-friendly conditions J. Chem. Sci 2020 132 1 8 https://dx.doi.org/10.1007/s12039-020-01776-3 10.1007/s12039-020-01776-3
Foroutan R. Mohammadi R. Taheri M. Ahmadi A. Ramavandi B. Edible waste oil to biofuel using reclaimable g-C3N4/HAp/Fe3O4/K2CO3 nanobiocomposite catalyst: Toxicity evaluation and optimization Environ. Technol. Innovation 2023 32 103403 https://dx.doi.org/10.1016/j.eti.2023.103403 10.1016/j.eti.2023.103403
Thomas A. Fischer A. Goettmann F. Antonietti M. Muller J. O. Schlogl R. Carlsson J. M. Graphitic carbon nitride materials: variation of structure and morphology and their use as metal-free catalysts J. Mater. Chem. 2008 18 41 4893 4908 https://dx.doi.org/10.1039/b800274f 10.1039/B800274F
Gibson K. Glaser J. Milke E. Marzini M. Tragl S. Binnewies M. Mayer H. A. Meyer H. J. Preparation of carbon nitride materials by polycondensation of the single-source precursor aminodichlorotriazine (ADCT) Mater. Chem. Phys. 2008 112 1 52 56 https://dx.doi.org/10.1016/j.matchemphys.2008.05.007 10.1016/j.matchemphys.2008.05.007
Liu L. Ma D. Zheng H. Li X. Cheng M. Bao X. Synthesis and characterization of microporous carbon nitride Microporous Mesoporous Mater. 2008 110 2-3 216 222 https://dx.doi.org/10.1016/j.micromeso.2007.06.012 10.1016/j.micromeso.2007.06.012
Wang X. Pan Z. Chemical changes and reaction mechanism of hardened cement paste-(NH4)2SO4-H2O system Constr. Build. Mater. 2017 152 434 443 https://dx.doi.org/10.1016/j.conbuildmat.2017.07.018 10.1016/j.conbuildmat.2017.07.018
Al Mamari S. Khudaish E. Kim Y. Khraisheh M. Selvaraj R. Lotus-bud like hexagonal ZnO/g-C3N4 composites for the photodegradation of benzene present in aqueous solution Inorg. Chem. Comm. 2023 150 110539 https://dx.doi.org/10.1016/j.inoche.2023.110539 10.1016/j.inoche.2023.110539
Chang F. Xie Y. Li C. Chen J. Luo J. Hu X. Shen J. A facile modification of g-C3N4 with enhanced photocatalytic activity for degradation of methylene blue Appl. Surf. Sci. 2013 280 967 974 https://dx.doi.org/10.1016/j.apsusc.2013.05.127 10.1016/j.apsusc.2013.05.127
Munusamy T. D. Yee C. S. Khan M. M. R. Construction of hybrid g-C3N4/CdO nanocomposite with improved photodegradation activity of RhB dye under visible light irradiation Adv. Powder. Technol. 2020 31 7 2921 2931 https://dx.doi.org/10.1016/j.apt.2020.05.017 10.1016/j.apt.2020.05.017
Buraidah M. H. Arof A. K. Characterization of chitosan/PVA blended electrolyte doped with NH4I J. Non-Cryst. Solids 2011 357 16-17 3261 3266 https://dx.doi.org/10.1016/j.jnoncrysol.2011.05.021 10.1016/j.jnoncrysol.2011.05.021
Konstas P. S. Konstantinou I. Petrakis D. Albanis T. Synthesis, characterization of g-C3N4/SrTiO3 heterojunctions and photocatalytic activity for organic pollutants degradation Catal. 2018 8 11 554 https://dx.doi.org/10.3390/catal8110554
Kumar R. Sudhaik A. Nguyen V. H. Van Le Q. Ahamad T. Thakur S. Hussain C. M. Singh P. Raizada P. Graphene oxide modified K, P co-doped g-C3N4 and CoFe2O4 composite for photocatalytic degradation of antibiotics J. Taiwan Inst. Chem. Eng. 2023 150 105077 https://dx.doi.org/10.1016/j.jtice.2023.105077 10.1016/j.jtice.2023.105077
Wang S. Li D. Sun C. Yang S. Guan Y. He H. Synthesis and characterization of g-C3N4/Ag3VO4 composites with significantly enhanced visible-light photocatalytic activity for triphenylmethane dye degradation Appl. Catal., B 2014 144 885 892 https://dx.doi.org/10.1016/j.apcatb.2013.08.008 10.1016/j.apcatb.2013.08.008
Zhurenok A. V. Potapenko K. O. Markovskaya D. V. Sidorenko N. D. Cherepanova S. V. Yu Gerasimov E. Saraev A. A. Kozlova E. A. Br-and I-modified g-C3N4 photocatalysts prepared via novel two-stage technique for hydrogen evolution and photocurrent generation Int. J. Hydrogen Energy 2024 51 1367 1379 https://dx.doi.org/10.1016/j.ijhydene.2023.09.195 10.1016/j.ijhydene.2023.09.195
Hári J. and Pukánszky B., Nanocomposites: preparation, structure, and properties, in Applied Plastics Engineering Handbook, 2011, pp. 109-142, DOI: https://dx.doi.org/10.1016/B978-1-4377-3514-7.10008-X
Elayadi H. Smietana M. Vasseur J. J. Balzarini J. Lazrek H. B. Synthesis of 1, 2, 3-Triazolyl Nucleoside Analogs as Potential Anti-I nfluenza A (H 3 N 2 Subtype) Virus Agents Archiv. Pharm. 2014 347 2 134 141 https://dx.doi.org/10.1002/ardp.201300260 10.1002/ardp.201300260 24272912
El Mansouri A. E. Oubella A. Mehdi A. AitItto M. Y. Zahouily M. Morjani H. Lazrek H. B. Design, synthesis, biological evaluation and molecular docking of new 1, 3, 4-oxadiazole homonucleosides and their double-headed analogs as antitumor agents Bioorg. Chem. 2021 108 104558 https://dx.doi.org/10.1016/j.bioorg.2020.104558 10.1016/j.bioorg.2020.104558 33358270
El Mansouri A. E. Oubella A. Maatallah M. AitItto M. Y. Zahouily M. Morjani H. Lazrek H. B. Design, synthesis, biological evaluation and molecular docking of new uracil analogs-1, 2, 4-oxadiazole hybrids as potential anticancer agents Bioorg. Med. Chem. Lett. 2020 30 19 127438 https://dx.doi.org/10.1016/j.bmcl.2020.127438 10.1016/j.bmcl.2020.127438 32736079
El Mansouri A. E. Maatallah M. Ait Benhassou H. Moumen A. Mehdi A. Snoeck R. Graciela A. Zahouily M. Lazrek H. B. Design, synthesis, chemical characterization, biological evaluation, and docking study of new 1,3,4-oxadiazole homonucleoside analogs Nucleosides, Nucleotides Nucleic Acids 2020 39 8 1088 1107 https://dx.doi.org/10.1080/15257770.2020.1761982 10.1080/15257770.2020.1761982 32397827
Ow G. Naung S. Iodotrimethylsilane a versatile synthetic reagent Tetrahedron 1982 38 15 2225 2277 https://dx.doi.org/10.1016/0040-4020(82)87002-6 10.1016/0040-4020(82)87002-6
Liang C. Ju W. Ding S. Sun H. Mao G. Effective synthesis of nucleosides utilizing O-Acetyl-Glycosyl chlorides as glycosyl donors in the absence of catalyst: mechanism revision and application to silyl-Hilbert-Johnson reaction Molecules 2017 22 1 84 https://dx.doi.org/10.3390/molecules22010084 10.3390/molecules22010084 28067759
Lazrek H. B. Taourirte M. Rochdi A. Redwane N. Ouzebla D. Baddi L. Sebti S. Vasseur J. J. Natural phosphate doped with KI in IN HMDS: A mild and efficient reagent for alkylation and glycosylation of nucleobaes Nucleosides, Nucleotides Nucleic Acids 2005 24 5-7 1093 1095 https://dx.doi.org/10.1081/ncn-200059179 10.1081/NCN-200059179 16248098
Baddi L. Smietana M. Sebti S. Vasseur J.-J. Lazrek H. B. A Procedure for facile synthesis of nucleosides Using N, O-Bis trimethylsilylacetamide in the presence of natural phosphate coated with potassium iodide Lett. Org. Chem. 2010 7 196 199 https://dx.doi.org/10.2174/157017810791112441 10.2174/157017810791112441
