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Pure Appl. Chem., 2000, Vol. 72, No. 7, pp. 1399-1403

http://dx.doi.org/10.1351/pac200072071399

Phase-transfer catalysis. A general green methodology in organic synthesis

Mieczyslaw Makosza

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warszawa, Poland

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  • Ananda Kumar T. Durai, Mohan P., Subrahmanyam C. V. S., Satyanarayana K.: Comparative Study of Catalytic Potential of TBAB, BTEAC, and CTAB in One-Pot Synthesis of 1,4-Dihydropyridines Under Aqueous Medium. Synthetic Communications 2014, 44, 574. <http://dx.doi.org/10.1080/00397911.2013.825807>
  • El-Sayed Ahmed M., Abd Allah Omyma A., El-Saghier Ahmed M. M., Mohamed Shaaban K.: Synthesis and Reactions of Five-Membered Heterocycles Using Phase Transfer Catalyst (PTC) Techniques. Journal of Chemistry 2014, 2014, 1. <http://dx.doi.org/10.1155/2014/163074>
  • Liang Theresa, Neumann Constanze N., Ritter Tobias: Einführung von Fluor und fluorhaltigen funktionellen Gruppen. Angew. Chem. 2013, 125, 8372. <http://dx.doi.org/10.1002/ange.201206566>
  • Liang Theresa, Neumann Constanze N., Ritter Tobias: Introduction of Fluorine and Fluorine-Containing Functional Groups. Angew. Chem. Int. Ed. 2013, 52, 8214. <http://dx.doi.org/10.1002/anie.201206566>
  • Sutter Marc, Dayoub Wissam, Métay Estelle, Raoul Yann, Lemaire Marc: 1,2,3-Trimethoxypropane and Glycerol Ethers as Bio-Sourced Solvents from Glycerol. Synthesis by Solvent-Free Phase-Transfer Catalysis and Utilization as an Alternative Solvent in Chemical Transformations. ChemCatChem 2013, 5, 2893. <http://dx.doi.org/10.1002/cctc.201300458>
  • Peljo Pekka, Qiao Liang, Murtomäki Lasse, Johans Christoffer, Girault Hubert H., Kontturi Kyösti: Electrochemically Controlled Proton-Transfer-Catalyzed Reactions at Liquid-Liquid Interfaces: Nucleophilic Substitution on Ferrocene Methanol. ChemPhysChem 2013, 14, 311. <http://dx.doi.org/10.1002/cphc.201200953>
  • Jimaré M.T., Cazaña F., Ramirez A., Royo C., Romeo E., Faria J., Resasco D.E., Monzón A.: Modelling of experimental vanillin hydrodeoxygenation reactions in water/oil emulsions. Effects of mass transport. Catalysis Today 2013, 210, 89. <http://dx.doi.org/10.1016/j.cattod.2012.11.015>
  • Magdycz Marta, Jarosz Sławomir: Synthesis of polyhydroxylated carbo-bicyclic compounds from sugar allyltins. Tetrahedron: Asymmetry 2013, 24, 1402. <http://dx.doi.org/10.1016/j.tetasy.2013.09.018>
  • de Freitas Martins Ernane, Pliego Josefredo Rodriguez: Unraveling the Mechanism of the Cinchoninium Ion Asymmetric Phase-Transfer-Catalyzed Alkylation Reaction. ACS Catal. 2013, 3, 613. <http://dx.doi.org/10.1021/cs400021r>
  • Benjamin Ilan: Recombination, Dissociation, and Transport of Ion Pairs across the Liquid/Liquid Interface. Implications for Phase Transfer Catalysis. J. Phys. Chem. B 2013, 117, 4325. <http://dx.doi.org/10.1021/jp306669t>
  • O'Brien Richard A., West Christy Wheeler, Hollingsworth Brian E., Stenson Alexandra C., Henderson Codey B., Mirjafari Arsalan, Mobarrez Niloufar, West Kevin N., Mattson Kaila M., Salter E. Alan, Wierzbicki Andrzej, Davis James H.: A simple and rapid route to novel tetra(4-thiaalkyl)ammonium bromides. RSC Adv. 2013, 3, 24612. <http://dx.doi.org/10.1039/c3ra44042g>
  • Alkorta Ibon, Elguero José, Gallo Roger: A theoretical study of the limits of the acidity of carbon acids in phase transfer catalysis in water and in liquid ammonia. cent.eur.j.chem. 2013, 11, 1711. <http://dx.doi.org/10.2478/s11532-013-0311-7>
  • Vogl Michael, Kratzer Regina, Nidetzky Bernd, Brecker Lothar: Candida tenuis Xylose Reductase Catalyzed Reduction of Aryl Ketones for Enantioselective Synthesis of Active Oxetine Derivatives. Chirality 2012, 24, 847. <http://dx.doi.org/10.1002/chir.22082>
  • Seebach Dieter, Beck Albert K., Bichsel Hans-Ulrich, Pichota Arkadius, Sparr Christof, Wünsch Ralf, Schweizer W. Bernd: Preparation and Characterization of New C2- and C1-Symmetric Nitrogen, Oxygen, Phosphorous, and Sulfur Derivatives and Analogs of TADDOL. Part III. HCA 2012, 95, 1303. <http://dx.doi.org/10.1002/hlca.201200148>
  • Vivekanand P.A., Wang Maw-Ling: An efficient recyclable polymer-supported bis-quaternary onium phase-transfer catalyst for the synthesis of dihalocyclopropyl derivatives at low alkaline concentration-comparative kinetic aspects. Catalysis Communications 2012, 22, 6. <http://dx.doi.org/10.1016/j.catcom.2012.02.010>
  • Yadav Ganapati D., Sowbna P.R.: Process intensification and waste minimization in liquid–liquid–liquid phase transfer catalyzed selective synthesis of mandelic acid. Chemical Engineering Research and Design 2012, 90, 1281. <http://dx.doi.org/10.1016/j.cherd.2012.01.007>
  • Wang Maw-Ling, Vivekanand P.A., Yu Ming-Chan: Hydrolysis of 4-methoxyphenylacetic acid butyl ester under liquid–liquid biphasic phase transfer condition and their kinetics. J TAIWAN INST CHEM E 2012, 43, 207. <http://dx.doi.org/10.1016/j.jtice.2011.10.005>
  • Pliego Josefredo R., Riveros Jose M.: New insights on reaction pathway selectivity promoted by crown ether phase-transfer catalysis: Model ab initio calculations of nucleophilic fluorination. Journal of Molecular Catalysis A: Chemical 2012, 363-364, 489. <http://dx.doi.org/10.1016/j.molcata.2012.07.030>
  • Eiberweiser Andreas, Buchner Richard: Ion-pair or ion-cloud relaxation? On the origin of small-amplitude low-frequency relaxations of weakly associating aqueous electrolytes. Journal of Molecular Liquids 2012, 176, 52. <http://dx.doi.org/10.1016/j.molliq.2012.03.025>
  • Santana Amanda S., Carvalho Diego B., Casemiro Nadla S., Hurtado Gabriela R., Viana Luiz H., Kassab Nájla M., Barbosa Sandro L., Marques Francisco A., Guerrero Palimécio G., Baroni Adriano C.M.: Improvement in the synthesis of (Z)-organylthioenynes via hydrothiolation of buta-1,3-diynes: a comparative study using NaOH or TBAOH as base. Tetrahedron Letters 2012, 53, 5733. <http://dx.doi.org/10.1016/j.tetlet.2012.08.003>
  • Sheydaei M., Kalaee M. R., Allahbakhsh A., Samar M., Aghili A., Dadgar M., Moosavi G. S.: Characterization of synthesized poly(aryldisulfide) through interfacial polymerization using phase-transfer catalyst. Journal of Sulfur Chemistry 2012, 33, 303. <http://dx.doi.org/10.1080/17415993.2012.662669>
  • Iliescu Smaranda, Avram Ecaterina, Visa Aurelia, Plesu Nicoleta, Popa Adriana, Ilia Gheorghe: New technique for the synthesis of polyphosphoesters. Macromol Res 2011, 19, 1186. <http://dx.doi.org/10.1007/s13233-011-1111-6>
  • Iliescu Smaranda, Plesu Nicoleta, Popa Adriana, Macarie Lavinia, Ilia Gheorghe: Green synthesis of polymers containing phosphorus in the main chain. Chim 2011, 14, 647. <http://dx.doi.org/10.1016/j.crci.2010.07.002>
  • Zucchi Claudia, Prampolini Giulio, Boese Roland, Caglioti Luciano, Alper Howard, Pályi Gyula: Intermediates of the PTC carbonylation of benzyl halides by cobalt carbonyls, II. J Organomet Chem 2011, 696, 1945. <http://dx.doi.org/10.1016/j.jorganchem.2010.09.041>
  • Potopnyk Mykhaylo A., Cmoch Piotr, Cieplak Maciej, Gajewska Agnieszka, Jarosz Sławomir: The synthesis of higher carbon sugars: a study on the rearrangement of higher sugar allylic alcohols. Tet Asymm 2011, 22, 780. <http://dx.doi.org/10.1016/j.tetasy.2011.04.021>
  • Nazario Carlos E.D., Santana Amanda S., Kawasoko Cristiane Y., Carollo Carlos A., Hurtado Gabriela R., Viana Luiz H., Barbosa Sandro L., Guerrero Palimécio G., Marques Francisco A., Dabdoub Vânia B., Dabdoub Miguel J., Baroni Adriano C.M.: Synthesis of (Z)-tributylstannyl enynes: systematic studies of Sonogashira cross-coupling reactions between (E)-1-iodovinyl-1-tributylstannanes and terminal acetylenes using amines or tetrabutylammonium hydroxide (TBAOH) as activator. Tetrahedron Letters 2011, 52, 4177. <http://dx.doi.org/10.1016/j.tetlet.2011.06.004>
  • Vivekanand P.A., Wang Maw-Ling: Sonocatalyzed synthesis of 2-phenylvaleronitrile under controlled reaction conditions – A kinetic study. Ultrasonics Sonochemistry 2011, 18, 1241. <http://dx.doi.org/10.1016/j.ultsonch.2011.02.002>
  • Wołosiak Agnieszka, Lewandowski Grzegorz, Milchert Eugeniusz: Catalytic Activity of H3PW12O40/Aliquat 336 in Epoxidation of (Z,E,E)-1,5,9-Cyclododecatriene to (E)-1,2-Epoxy-(Z,E)-5,9-Cyclododecadiene. Ind Eng Chem Res 2011, 50, 7101. <http://dx.doi.org/10.1021/ie1021738>
  • Collis Alana E. C., Horváth István T.: Heterogenization of homogeneous catalytic systems. Catal Sci Technol 2011, 1, 912. <http://dx.doi.org/10.1039/c1cy00174d>
  • Hu Yu Lin, Jiang Hui, Lu Ming: Efficient and convenient C-3 functionalization of indoles through Ce(OAc)3/TBHP-mediated oxidative C–H bond activation in the presence of β-cyclodextrin. Green Chem 2011, 13, 3079. <http://dx.doi.org/10.1039/c1gc15639j>
  • Iliescu Smaranda, Grozav Ion, Funar-Timofei Simona, Plesu Nicoleta, Popa Adriana, Ilia Gheorghe: Optimization of synthesis parameters in interfacial polycondensation using design of experiments. Polym Bull 2010, 64, 303. <http://dx.doi.org/10.1007/s00289-009-0212-2>
  • Orlova Anna V., Shpirt Anna M., Kulikova Nadezhda Y., Kononov Leonid O.: N,N-Diacetylsialyl chloride—a novel readily accessible sialyl donor in reactions with neutral and charged nucleophiles in the absence of a promoter. Carbohydrates Research 2010, 345, 721. <http://dx.doi.org/10.1016/j.carres.2010.01.005>
  • Riccaboni Mauro, La Porta Elena, Martorana Andrea, Attanasio Roberta: Effect of phase transfer chemistry, segmented fluid flow, and sonication on the synthesis of cinnamic esters. Tetrahedron 2010, 66, 4032. <http://dx.doi.org/10.1016/j.tet.2010.04.031>
  • Bohström Zebastian, Rico-Lattes Isabelle, Holmberg Krister: Oxidation of cyclohexene into adipic acid in aqueous dispersions of mesoporous oxides with built-in catalytical sites. Green Chem 2010, 12, 1861. <http://dx.doi.org/10.1039/c0gc00032a>
  • Ābele E., Ābele R., Golomba Ļ., Rubina K., Višņevska J., Beresņeva T.: "Green Chemical" Methods for the Regioselective Synthesis of 1-Hetarylsulfanyl-ω-Cyanoalkanes. Latvian Journal of Chemistry 2010, 49, 278. <http://dx.doi.org/10.2478/v10161-010-0006-8>
  • Esen Ilker, Yolacan Cigdem, Aydogan Feray: Long Chain Dicationic Phase Transfer Catalysts in the Condensation Reactions of Aromatic Aldehydes in Water Under Ultrasonic Effect. Bulletin of the Korean Chemical Society 2010, 31, 2289. <http://dx.doi.org/10.5012/bkcs.2010.31.8.2289>
  • Borovinskaya E. S., Mammitzsch L., Uvarov V. M., Schael F., Reschetilowski W.: Experimental Investigation and Modeling Approach of the Phenylacetonitrile Alkylation Process in a Microreactor. Chem Eng Technol 2009, 32, 919. <http://dx.doi.org/10.1002/ceat.200800672>
  • López-Fonseca R., González-Marcos M. P., González-Velasco J. R., Gutiérrez-Ortiz J. I.: A kinetic study of the depolymerisation of poly(ethylene terephthalate) by phase transfer catalysed alkaline hydrolysis. J Chem Technol Biotechnol 2009, 84, 92. <http://dx.doi.org/10.1002/jctb.2011>
  • Kalaee M. R., Famili M. H. N., Mahdavi H.: Synthesis and Characterization of Polysulfide Rubber Using Phase Transfer Catalyst. Macromol Symp 2009, 277, 81. <http://dx.doi.org/10.1002/masy.200950310>
  • Chelli Saloua, Majdoub Mustapha, Aeiyach Salah, Jouini Mohamed: Polyrotaxanes based on polyethers and β-cyclodextrin. J Polym Sci A Polym Chem 2009, 47, 4391. <http://dx.doi.org/10.1002/pola.23492>
  • Chakrabarty Manas, Karmakar Sulakshana, Mukherjee Ratna, Arima Shiho, Harigaya Yoshihiro: A mild and expedient one-pot synthesis of substituted benzimidazoles in water using a phase-transfer catalyst. Monatshefte für Chemie 2009, 140, 375. <http://dx.doi.org/10.1007/s00706-008-0036-z>
  • Vivekanand P.A., Balakrishnan T.: Synthesis and characterization of a novel multi-site phase transfer catalyst and a kinetic study of the intramolecular cyclopentanation of indene. CATAL A GENERAL 2009, 364, 27. <http://dx.doi.org/10.1016/j.apcata.2009.05.014>
  • Abronina Polina I., Kachala Vadim V., Kononov Leonid O.: A novel synthesis of β-d-mannopyranosyl azide by phase transfer catalysis. Carbohydrates Research 2009, 344, 240. <http://dx.doi.org/10.1016/j.carres.2008.10.027>
  • Gupta Neeraj, Kad Goverdhan L., Singh Jasvinder: Enhancing nucleophilicity in ionic liquid [bmim]HSO4: A recyclable media and catalyst for the halogenation of alcohols. Journal of Molecular Catalysis A 2009, 302, 11. <http://dx.doi.org/10.1016/j.molcata.2008.11.040>
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  • Nelson Katherine V., Benjamin Ilan: Microhydration effects on a model S[sub N]2 reaction in a nonpolar solvent. J Chem Phys 2009, 130, 194502. <http://dx.doi.org/10.1063/1.3138902>
  • Yoganand K. S., Vidhya K. R., Umapathy M. J.: Phase Transfer Catalyst-Induced Free Radical Polymerization of Acrylonitrile Using Water Soluble Initiator – A Kinetic Study. Int J Polym Mater 2009, 58, 355. <http://dx.doi.org/10.1080/00914030902852278>
  • Kryshtal Galina V., Zhdankina Galina M., Zlotin Sergei G.: Recoverable Phase-Transfer Catalysts with Fluorinated Anions: Generation and Reactions of Dichlorocarbene and CCl3 Anion in the Heterogeneous System KOH(s)/CHCl3/nBu4NPF6. Eur J Org Chem 2008, 2008, 1777. <http://dx.doi.org/10.1002/ejoc.200701034>
  • Iliescu Smaranda, Grozav Ion, Plesu Nicoleta, Pascariu Aurelia, Ilia Gheorghe: Design of experiments applied to the study of the reaction between phenylphosphonic dichloride with bisphenol by inverse phase transfer catalysis method. Polym Eng Sci 2008, 48, 1304. <http://dx.doi.org/10.1002/pen.21097>
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  • Abass Mohamed, Mayas Aisha S.: Substituted pyridopyrimidinones, 1: Convenient PTC alkylation and halogenation of 2-hydroxy-4H-pyrido[1,2-a]pyrimidin-4-one. Heteroatom Chem 2007, 18, 19. <http://dx.doi.org/10.1002/hc.20245>
  • Singh Vijay, Pathak Richa, Batra Sanjay: Significant yield improvement in the stereoselective synthesis of allyl cyanides from Baylis–Hillman derivatives in aqueous medium under the influence of the phase-transfer catalyst. Catal Commun 2007, 8, 2048. <http://dx.doi.org/10.1016/j.catcom.2007.03.032>
  • Chinchilla Rafael, Nájera Carmen, Ortega Francisco J.: Improved conditions for the asymmetric synthesis of α-amino acids using Cinchona-derived anthracenylmethyl ammonium salts as chiral phase-transfer organocatalysts. Tet Asymm 2006, 17, 3423. <http://dx.doi.org/10.1016/j.tetasy.2006.12.004>
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  • Wang Maw-Ling, Hsu Shu-Li, Hsieh Yu-Ming: SYNTHESIS OF DIALKOXYMETHANE AT HIGH ALKALINE CONCENTRATION VIA PHASE TRANSFER CATALYSIS. Chem Eng Com 2006, 193, 1368. <http://dx.doi.org/10.1080/00986440500511379>
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  • Dekamin Mohammad G., Mallakpour † Shadpour, Ghassemi Maryam: Combination of Sulfite Anion and Phase Transfer Catalysts for Green Cyclotrimerization of Aryl Isocyanates. Synth Common 2005, 35, 427. <http://dx.doi.org/10.1081/SCC-200048951>
  • Chinchilla Rafael, Mazón Patricia, Nájera Carmen, Ortega Francisco J.: The counterion effect in the phase-transfer catalyzed asymmetric synthesis of α-amino acids promoted by anthryl-derived dimeric Cinchona ammonium salts. Tet Asymm 2004, 15, 2603. <http://dx.doi.org/10.1016/j.tetasy.2004.07.025>
  • Watanabe Yasunobu, Fuji Takako, Hioki Kazuhito, Tani Shohei, Kunishima Munetaka: Development of a Simple System for Dehydrocondensation Using Solid-Phase Adsorption of a Water-Soluble Dehydrocondensing Reagent (DMT-MM). Chem Pharm Bull 2004, 52, 1223. <http://dx.doi.org/10.1248/cpb.52.1223>
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