A Green and Efficient Solvent- and Catalyst-Free Ultrasonic Dibenzylation Procedure
Affiliation:
1 SavehUniversityofMedicalSciences, SavehIran
2 DepartmentofOrganicChemistry, FacultyofChemistry, Bu-AliSinaUniversity, Hamedan, Iran
3 ActivePharmaceuticalIngredientsResearchCenter, PharmaceuticalSciencesBranch,
IslamicAzadUniversity (IAUPS), Tehran, Iran
somi.heydari@gmail.com; davood.habibi@gmail.com
DOI:
https://doi.org/10.23939/chcht16.01.126
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Keywords:
Abstract:
A greener improvement was achieved for the synthesis of diverse N,N-dibenzylated compounds from the reaction of various aromatic amines with benzyl bromide using the ultrasound irradiation in solvent- and catalyst-free conditions. The dibenzylation reactions were carried out in different solvents and solvent-free conditions under ultrasound irradiation at various temperatures. The yields were very low in all applied solvents, while in the solvent-free condition and at room temperature, the yields were excellent. Due to obtaining the high reaction yields, the catalyst was not used.
References:
[1] Anand, Ch.; Priya, S.V.; Lawrence, G.;Dhawale, D.S.;Varghese, S.;Wahab, M.A.;Prasad, K.S.; Vinu, A. Cage Type Mesoporous Ferrosilicate Catalysts with 3D Structure for Benzylation of Aromatics.Catal. Today2013, 204, 125-131. https://doi.org/10.1016/j.cattod.2012.08.010
https://doi.org/10.1016/j.cattod.2012.08.010
[2] Wang, H.; Ma, Y.; Tian, H.;Yu, A.;Chang, J.; Wu, Y. TetrabutylAmmonium Bromide-Mediated Benzylation of Phenols in Water under Mild Condition.Tetrahedron2014, 70, 2669-2673. https://doi.org/10.1016/j.tet.2014.01.004
https://doi.org/10.1016/j.tet.2014.01.004
[3] Cuong, N.D.;Hoa, N.D.;Hoa, T.T.;Khieu, D.Q.;Quang, D.T.;Quang, V.V.; Hieu, N.V.NanoporousHematite Nanoparticles: Synthesis and Applications for Benzylation of Benzene and Aromatic Compounds.J. Alloy. Compd. 2014, 582, 83-87. https://doi.org/10.1016/j.jallcom.2013.08.057
https://doi.org/10.1016/j.jallcom.2013.08.057
[4] Saxena, S.K.;Viswanadham,N. Enhanced Catalytic Properties of Mesoporous Mordenite for Benzylation of Benzene with Benzyl Alcohol.Appl. Surf. Sci. 2017, 392, 384-390. https://doi.org/10.1016/j.apsusc.2016.09.062
https://doi.org/10.1016/j.apsusc.2016.09.062
[5] Yuan, B.; Li, Y.; Wang, Z.; Yu, F.;Xie, C.; Yu, S. A Novel Brønsted-Lewis Acidic Catalyst Based on Heteropoly Phosphotungstates: Synthesis and Catalysis in Benzylation of p-Xylene with Benzyl Alcohol.Mol. Catal. 2017, 443, 110-116. https://doi.org/10.1016/j.mcat.2017.10.003
https://doi.org/10.1016/j.mcat.2017.10.003
[6] Bhadra, K.H.; Yadav, G.D. Atom Economical Benzylation of Phenol with Benzyl Alcohol Using 20 % (w/w)Cs2.5H0.5PW12O40 Supported on Mesocellular Foam Silica (MCF) and its Kinetics.Micropor. Mesopor. Mat. 2018, 263, 190-200. https://doi.org/10.1016/j.micromeso.2017.12.017
https://doi.org/10.1016/j.micromeso.2017.12.017
[7] Pu, X.;Su, Y. Heterogeneous Catalysis in Microreactors with Nanofluids for Fine Chemicals Syntheses: Benzylation of Toluene with Benzyl Chloride over Silica-Immobilized FeCl3 Catalyst.Chem. Eng. Sci. 2018, 184, 200-208. https://doi.org/10.1016/j.ces.2018.03.049
https://doi.org/10.1016/j.ces.2018.03.049
[8] Nair, D.S.; Kurian, M. Highly Selective Synthesis of Diphenyl Methane via Liquid Phase Benzylation of Benzene over Cobalt Doped Zinc Nanoferrite Catalysts at Mild Conditions.J. Saudi Chem. Soc. 2019, 23, 127-132. https://doi.org/10.1016/j.jscs.2018.05.011
https://doi.org/10.1016/j.jscs.2018.05.011
[9] Mishra, K.; Lee, Y.R. Highly Synergistic Effect of Bifunctional Ru-rGO Catalyst for Enhanced Hydrogenative-Reductive Benzylation of N-Heteroaromatics.J. Catal. 2019, 376, 77-86. https://doi.org/10.1016/j.jcat.2019.06.052
https://doi.org/10.1016/j.jcat.2019.06.052
[10] Dar, B.A.;Shrivastava, V.;Bowmik, A.;Wagay, M.A.; Singh, B. An Expeditious N,N-Dibenzylation of Anilines under Ultrasonic Irradiation Conditions Using Low Loading Cu(II)-Clay Heterogeneous Catalyst.Tetrahedron Lett. 2014, 56, 136-141. https://doi.org/10.1016/j.tetlet.2014.11.044
https://doi.org/10.1016/j.tetlet.2014.11.044
[11] Fueno, T.; Okamoto, H.; Tsuruta, T.; Furukawa, J. Quaternary Ammonium Salt as Initiator for Vinyl Polymerization.J. Polym. Sci. 1959, 36, 407-420. https://doi.org/10.1002/pol.1959.1203613034
https://doi.org/10.1002/pol.1959.1203613034
[12] Gupta, M.; Paul, S.; Gupta, R. SiO2-Cu2O: An Efficient and Recyclable Heterogeneous Catalyst for N-Benzylation of Primary and Secondary Amines.Chinese J. Catal. 2014, 35, 444-450. https://doi.org/10.1016/S1872-2067(14)60009-7
https://doi.org/10.1016/S1872-2067(14)60009-7
[13] Major,R.T.CatalyticReduction of Mixtures of Para-Nitro- and Nitrosophenols with Aldehydes and Ketones. J. Am. Chem. Soc.1931, 53, 1901-1908. https://doi.org/10.1021/ja01356a042
https://doi.org/10.1021/ja01356a042
[14] Hayat, S.; Atta-ur-Rahman; Choudhary, M.I.;Khan, K.M.;Schumann, W.; Bayer, E.N-Alkylation of Anilines, Carboxamides and Several Nitrogen Heterocycles Using CsF-Celite/Alkyl Halides/CH3CN Combination.Tetrahedron2001, 57, 9951-9957. https://doi.org/10.1016/S0040-4020(01)00989-9
https://doi.org/10.1016/S0040-4020(01)00989-9
[15] Leoppky, R.N.;Tomasik, W.Stereoelectronic Effects in Tertiary Amine Nitrosation: Nitrosative Cleavage vs. Aryl Ring Nitration.J. Org. Chem. 1983, 48, 2751-2757. https://doi.org/10.1021/jo00164a023
https://doi.org/10.1021/jo00164a023
[16] Saitoh, T.; Ichikawa, J. Bis(triarylmethylium)-Mediated Diaryl Ether Synthesis: Oxidative Arylation of Phenols with N,N-Dialkyl-4-phenylthioanilines.J. Am. Chem. Soc. 2005, 127, 9696-9697. https://doi.org/10.1021/ja051839n
https://doi.org/10.1021/ja051839n
[17] Li, Ch.; Wan, K.-F.; Guo, F.-Y.; Wu, Q.-H.; Yuan, M.-L.; Li, R.-X.; Fu, H.-Y.; Zheng, X.-L.; Chen, H. Iridium-Catalyzed Alkylation of Amine and Nitrobenzene with Alcohol to Tertiary Amine under Base- and Solvent-Free Conditions.J. Org Chem. 2019, 84, 2158-2168. https://doi.org/10.1021/acs.joc.8b03137
https://doi.org/10.1021/acs.joc.8b03137
[18] Noori, S.;Ghorbani-Vaghei, R.; Mirzaei-Mosbat, M.N-Benzylation of Primary Amines Using Magnetic Fe3O4 Nanoparticles Functionalized with Hexamethylenetetramine as an Efficient and Recyclable Heterogeneous Catalyst.J. Mol. Struct. 2020, 1219, 128583. https://doi.org/10.1016/j.molstruc.2020.128583
https://doi.org/10.1016/j.molstruc.2020.128583
[19] Peng, Q.; Zhang, Y.; Shi, F.; Deng, Y. Fe2O3-Supported Nano-Gold Catalyzed One-Pot Synthesis of N-Alkylated Anilines from Nitroarenes and Alcohols.Chem. Commun. 2011, 47, 6476-6478. https://doi.org/10.1039/c1cc11057h
https://doi.org/10.1039/c1cc11057h
[20] Safaei-Ghomi, J.;Nazemzadeh, S.H.;Shahbazi-Alavi, H. Preparation and Characterization of Fe3O4@SiO2/APTPOSS Core-Shell Composite Nanomagnetics as a Novel Family of Reusable Catalysts and Their Application in the One-Pot Synthesis of 1,3-Thiazolidin-4-one Derivatives.Appl. Organometal Chem. 2016, 30, 911-916. https://doi.org/10.1002/aoc.3520
https://doi.org/10.1002/aoc.3520
[21] Eddingsaas, N.;Suslick, K. Light from Sonication of Crystal Slurries.Nature2006, 444, 163. https://doi.org/10.1038/444163a
https://doi.org/10.1038/444163a
[22] Khaligh, N.G., Shirini, F.N-Sulfonic Acid Poly(4-vinylpyridinium) Hydrogen Sulfate as an Efficient and Reusable Solid Acid Catalyst for One-Pot Synthesis of Xanthene Derivatives in Dry Media under Ultrasound Irradiation.Ultrason. Sonochem. 2015, 22, 397-403. https://doi.org/10.1016/j.ultsonch.2014.06.020
https://doi.org/10.1016/j.ultsonch.2014.06.020
[23] Ramazani, A.; Rouhani, M.;Joo, S.W. Catalyst-Free Sonosynthesis of Highly Substituted Propanamide Derivatives in Water.Ultrason. Sonochem. 2016, 28, 393-399. https://doi.org/10.1016/j.ultsonch.2015.08.019
https://doi.org/10.1016/j.ultsonch.2015.08.019
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