Synthesis of Benzyl Vinyl Ethers Through a Domino Reaction of Benzyl Alcohols with Dimethyl Sulfoxide in the Presence of Arginine and Potassium Hydroxide Without the Use of Metallic Catalysts

Document Type : Research Article

Authors

Department of Chemistry, Ilam University, Ilam, I.R. IRAN

Abstract

Herein, a one-pot, new, and domino method for the synthesis of benzyl vinyl ethers without the use of a metallic catalyst in the presence of arginine and dimethyl-sulfoxide has been reported. Arginine, as an inexpensive and available amino acid, has contributed to the advancement of this reaction. Dimethyl sulfoxide, in addition to the reaction solvent, is effective as a carbon source in the synthesis of benzyl vinyl ethers. Under optimal reaction conditions, a series of benzyl vinyl ether derivatives was synthesized from good to excellent yields and at relatively convenient times. High efficiency (87-87%), easy separation, cheap and affordable materials, cost-effectiveness in terms of time and cost and low-cost reactants are the most important advantages of these reactions.

Keywords

Main Subjects


[1] Tejedor D., Méndez‐Abt G., Cotos L., Ramirez M.A., García‐Tellado F.A., A Microwave‐Assisted Domino Rearrangement of Propargyl Vinyl Ethers to Multifunctionalized Aromatic Platforms, Chem. A. Eur. J17(12): 3318-3321 (2011).
[3] Shade R.E., Hyde A.M., Olsen J.C., Merlic C.A., Copper-Promoted Coupling of Vinyl Boronates and Alcohols: A Mild Synthesis of Allyl Vinyl Ethers, J. Am. Chem. Soc132(4): 1202-1203 (2010).
[4]  Stockland, R., "Practical Functional Group Synthesis", John Wiley & Sons, Inc., New Jersy, (2016).
[5] Tejedor D., Cotos L., García-Tellado F., Microwave-Assisted Domino Access to C2-Chain Functionalized Furans from Tertiary Propargyl Vinyl EthersOrg. Lett13(16): 4422-4425 (2011).
[6]  Méndez Abt G., "Propargyl Vinyl Ethers: Synthetic Applications", Universidad de La Laguna, Servicio de Publicaciones (2014). 
[7]  Foster D.J., Tobler E., Organomercury Chemistry. A Novel Synthesis of Vinyl Esters, Vinyl Ethers and Vinyl Thioethers, J. Am. Chem. Soc. 83(4): 851-855(1961).
[8] Kadzimirsz D., Kramer D., Sripanom L., Oppel I.M., Rodziewicz P., Doltsinis N.L., Dyker G., A Domino Annulation Reaction under Willgerodt− Kindler Conditions,  J. Org. Chem. 73(12): 4644-4649 (2008).
[9] Tietze L.F., Brasche G., Gericke K., „Domino Reactions in Organic Synthesis“. Wiley-VCH., Weinheim ‏ (2006).
[10] معادی، تارا؛ قهرمان زاده، رامین؛ یوسفی، مریم؛ محمدی، فرشته، تهیه نانوذره­های نقره توسط عصاره چهار گونه گیاهی و بررسی ویژگی­های ضد میکروبی آن، نشریه شیمی و مهندسی شیمی ایران. (4)33: 1تا9(1393).      
[11] (a) Cho C.G., Feit B.A., Webster O.W., Initiation of Vinyl Ether Polymerization by Trimethylsilyl Triflate, Dimethyl Sulfide, and Adventitious WaterMacromolecules.  25(8), 2081-2085 (1992).    
         (b) Bordwell FG., Equilibrium Acidities in Dimethyl Sulfoxide SolutionAccounts. Chem. Res21(12): 456–463 (1988).
[12] (a) Epstein W.W., Sweat F.W., Dimethyl Sulfoxide OxidationsChem. Rev. 67 (3):247–260(1967).   
       (b)Tidwell T.T., Oxidation of Alcohols by Activated Dimethyl Sulfoxide and Related Reactions: An Update,  Synthesis.  10: 857–870 (1990).
[13] Wu X.F., Natte K., The Applications of Dimethyl Sulfoxide as Reagent in Organic Synthesis,  Adv. Synth. Catal358(3): 336-352 (2016).  
[14] Alligaris M., Structure and Bonding in Metal Sulfoxide Complexes: An Update. Coordin. Chem. Rev248 (3–4): 351–375 (2004).
[15] Ansari S.A.M.K. , Ficiarà E., Ruffinatti F.A., Stura I., Argenziano M., Abollino O., D’Agata F., Magnetic Iron Oxide Nanoparticles: Synthesis, Characterization and Functionalization for Biomedical Applications in the Central Nervous SystemMaterials12(3): 465 (2019).
[16 ] (a) Liu Y.F., Ji P.Y., Xu J.W., Hu Y.Q., Liu Q., Luo W.P., & Guo C.C., Transition Metal-Free α-Csp3-H Methylenation of Ketones to form C=C Bond Using Dimethyl Sulfoxide as Carbon Source J. Org. Chem. 82(14): 7159-7164 (2017). 
          (b) Yu Z.W., Quinn P.J.,  Dimethyl Sulphoxide: A Review of Its Applications in Cell BiologyBio. Reports. 14(6): 259-281 (1994).
[17] Winternheimer D.J., Shade R.E., Merlic C.A., Methods for Vinyl Ether SynthesisSynthesis. 15: 2497-2511 (2010).
[18] خانلری، طیبه، تهیه پلیمر حمایت کننده پالادیوم، برپایه پلی وینیل الکل و استفاده از آن در واکنش هِک، نشریه شیمی و مهندسی شیمی ایران. (2)34 : 25تا40 (1394).
[19] Nurmanov S.E., Gevorgyan A.M., Matmuratov S.A., Kasimova O., Sirlibaev T.S., Kalyadin V.G., Synthesis of Vinyl Phenyl Ether and Its Use for Ammetric Titration of Silver (I), Russ. J. Appl. Chem. 75(3): 480-482 (2002).
[20] Yang K., Song Q., Styryl Ether Formation from Benzyl Alcohols Under Transition-Metal-Free Basic DMSO Conditions, Org.  & Bio. Chem13(8): 2267-2272 (2015).
[21] Okimoto Y., Sakaguchi S., Ishii Y., Development of a Highly Efficient Catalytic Method for Synthesis of Vinyl Ethers,  J. Am. Chem. Soc124(8): 1590-1591 (2002).
[22] (a) Xi Y., Dong B., Shi X., Ambient Gold-Catalyzed O-Vinylation of Cyclic 1, 3-Diketone:  A Vinyl Ether  SynthesisBeilstein. J. Org. Chem. 9(1): 2537-2543 (2013).   
       (b) Kuram M.R., Bhanuchandra M., Sahoo A.K., Gold-Catalyzed Intermolecular Hydrophenoxylation of Unactivated Internal Alkynes J. Org . Chem. 75(7): 2247-2258 (2010).
[23]  Handerson S., Schlaf M., Palladium (II)-Catalyzed Transfer Vinylation of Protected Monosaccharides, Org. Lett4(3): 407-409 (2002).
[24]  Crivello J.V., Kong S., Efficient Isomerization of Allyl Ethers and Related Compounds Using Pentacarbonyliron J. Org. Chem. 63(19): 6745-6748 (1998).
[25]  Zhang Q., Cai S., Li L., Chen Y., Rong H., Niu Z., Li Y., Direct Syntheses of Styryl Ethers from Benzyl Alcohols via Ag Nanoparticle-Catalyzed Tandem Aerobic OxidationACS. Catal3(7): 1681-1684 (2013).
[26] Gilbert J.C., Weerasooriya U., Generation of Aldehydic Enol Ethers and Enamines by Olefination of Ketones, J. Org. Chem. 48(4): 448-453 (1983).
[28] Matake R., Adachi Y., Matsubara H., Synthesis of Vinyl Ethers of Alcohols Using Calcium Carbide Under Super Basic Catalytic Conditions (KOH/DMSO)Green. Chem. 18(9): 2614-2618 (2016).