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Pure Appl. Chem., 2000, Vol. 72, No. 7, pp. 1373-1380

http://dx.doi.org/10.1351/pac200072071373

Green Lewis acid catalysis in organic synthesis

Shū Kobayashi and Kei Manabe

Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

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  • Jerez Javier, Isaguirre Andrea C., Bazán Cristian, Martinez Luis D., Cerutti Soledad: Determination of scandium in acid mine drainage by ICP-OES with flow injection on-line preconcentration using oxidized multiwalled carbon nanotubes. Talanta 2014, 124, 89. <http://dx.doi.org/10.1016/j.talanta.2014.02.028>
  • Rajaguru Kandasamy, Suresh Rajendran, Mariappan Arumugam, Muthusubramanian Shanmugam, Bhuvanesh Nattamai: Erbium Triflate Promoted Multicomponent Synthesis of Highly Substituted Imidazoles. Org. Lett. 2014, 16, 744. <http://dx.doi.org/10.1021/ol403456b>
  • Zhang Tao, Zhang Yunxiao, Li Zaichun, Song Zhongtai, Liu Hao, Tao Jingchao: Direct Asymmetric Aldol Reaction Co-catalyzed by Amphiphilic Prolinamide Phenol and Lewis Acidic Metal on Water. Chin. J. Chem. 2013, 31, 247. <http://dx.doi.org/10.1002/cjoc.201201017>
  • Dadiboyena Sureshbabu, Hamme Ashton T.: Environmentally Benign Lewis Acid Promoted [2+3] Dipolar Cycloaddition Reactions of Nitrile Imines with Alkenes in Water. Eur. J. Org. Chem. 2013, 2013, 7567. <http://dx.doi.org/10.1002/ejoc.201300840>
  • Mulik Abhijeet, Chandam Dattatraya, Patil Prasad, Patil Dayanand, Jagdale Suryabala, Deshmukh Madhukar: Proficient synthesis of quinoxaline and phthalazinetrione derivatives using [C8dabco]Br ionic liquid as catalyst in aqueous media. Journal of Molecular Liquids 2013, 179, 104. <http://dx.doi.org/10.1016/j.molliq.2012.12.006>
  • Pereira Rui F. P., Valente Artur J. M., Burrows Hugh D., de Zea Bermudez Verónica, Carvalho Rui A., Castro Ricardo A. E.: Structural characterization of solid trivalent metal dodecyl sulfates: from aqueous solution to lamellar superstructures. RSC Adv. 2013, 3, 1420. <http://dx.doi.org/10.1039/c2ra21906a>
  • Qiao Yupu, Headley Allan D.: A simple and highly effective water-compatible organocatalytic system for asymmetric direct Michael reactions of linear aldehydes to maleimides. Green Chem. 2013, 15, 2690. <http://dx.doi.org/10.1039/c3gc41024b>
  • Asta Chimène, Schmidt Dietmar, Conrad Jürgen, Frey Wolfgang, Beifuss Uwe: Combination of enzyme- and Lewis acid-catalyzed reactions: a new method for the synthesis of 6,7-dihydrobenzofuran-4(5H)-ones starting from 2,5-dimethylfuran and 1,3-cyclohexanediones. Org. Biomol. Chem. 2013, 11, 5692. <http://dx.doi.org/10.1039/c3ob40926k>
  • Pourali Ali Reza, Ghayeni Samaneh, Afghahi Fatemeh: Efficient and Regioselective Ring-Opening of Epoxides with Alcohols and Sodium Azide by using Catalytic Amounts of GaCl3/Polyvinylpyrrolidone. Bulletin of the Korean Chemical Society 2013, 34, 1741. <http://dx.doi.org/10.5012/bkcs.2013.34.6.1741>
  • Qiao Yupu, He Junpeng, Ni Bukuo, Headley Allan D.: Asymmetric Michael Reaction of Acetaldehyde with Nitroolefins Catalyzed by Highly Water-Compatible Organocatalysts in Aqueous Media. Adv. Synth. Catal. 2012, 354, 2849. <http://dx.doi.org/10.1002/adsc.201200215>
  • Kobayashi Shū, Xu Pengyu, Endo Toshimitsu, Ueno Masaharu, Kitanosono Taku: Chiral Copper(II)-Catalyzed Enantioselective Boron Conjugate Additions to α,β-Unsaturated Carbonyl Compounds in Water. Angew. Chem. 2012, 124, 12935. <http://dx.doi.org/10.1002/ange.201207343>
  • Kobayashi Shū, Xu Pengyu, Endo Toshimitsu, Ueno Masaharu, Kitanosono Taku: Chiral Copper(II)-Catalyzed Enantioselective Boron Conjugate Additions to α,β-Unsaturated Carbonyl Compounds in Water. Angew. Chem. Int. Ed. 2012, 51, 12763. <http://dx.doi.org/10.1002/anie.201207343>
  • Chen Guodong, Fu Xiangkai, Li Chao, Wu Chuanlong, Miao Qiang: Highly efficient direct a larger-scale aldol reactions catalyzed by a flexible prolinamide based-metal Lewis acid bifunctional catalyst in the presence of water. J Organomet Chem 2012, 702, 19. <http://dx.doi.org/10.1016/j.jorganchem.2011.12.006>
  • Tran Phuong Hoang, Duus Fritz, Le Thach Ngoc: Friedel–Crafts acylation using bismuth triflate in [BMI][PF6]. Tetrahedron Letters 2012, 53, 222. <http://dx.doi.org/10.1016/j.tetlet.2011.11.022>
  • Gohain Mukut, Marais Charlene, Bezuidenhoudt Barend C.B.: Al(OTf)3: an efficient recyclable catalyst for direct nucleophilic substitution of the hydroxy group of propargylic alcohols with carbon- and heteroatom-centered nucleophiles to construct C–C, C–O, C–N and C–S bonds. Tetrahedron Letters 2012, 53, 1048. <http://dx.doi.org/10.1016/j.tetlet.2011.12.060>
  • Pericherla Kasiviswanadharaju, Khungar Bharti, Kumar Anil: One-pot, three-component synthesis of 1-amidomethyl-imidazo[1,2-a]pyridines catalyzed by ytterbium triflate. Tetrahetron Lett 2012, 53, 1253. <http://dx.doi.org/10.1016/j.tetlet.2011.12.121>
  • Gohain Mukut, Marais Charlene, Bezuidenhoudt Barend C.B.: An Al(OTf)3-catalyzed environmentally benign process for the propargylation of indoles. Tetrahedron Letters 2012, 53, 4704. <http://dx.doi.org/10.1016/j.tetlet.2012.06.095>
  • Swanson Claudia H., Shaikh Harris A., Abdollahian Yashar, Hauser Jesse L., Ikehata Mariko, Oliver Scott R. J.: Control of Morphology and Catalytic Activity of a Cationic Layered Material. Growth Des 2012, 12, 93. <http://dx.doi.org/10.1021/cg200826d>
  • Maity Arnab Kumar, Roy Sujit: A Multimetallic Piano-Stool Ir–Sn3 Catalyst for Nucleophilic Substitution Reaction of γ-Hydroxy Lactams through N-Acyliminium Ions. J Org Chern 2012, 77, 2935. <http://dx.doi.org/10.1021/jo202359e>
  • Kolvari Eskandar, Zolfigol Mohammad Ali, Peiravi Marjan: Green synthesis of quinoxaline derivatives using p-dodecylbenzensulfonic acid as a surfactant-type Bronsted acid catalyst in water. Green Chem Lett & Revs 2012, 5, 155. <http://dx.doi.org/10.1080/17518253.2011.606849>
  • Kumar Anil, Rao M. Sudershan: An expeditious and greener one-pot synthesis of 4H-chromenes catalyzed by Ba(OTf)2 in PEG-water. Green Chemistry Letters and Reviews 2012, 5, 283. <http://dx.doi.org/10.1080/17518253.2011.623683>
  • Chintala Poornima, Ghosh Subrata K., Long Elizabeth, Headley Allan D., Ni Bukuo: The Application of a Recyclable Organocatalytic System to the Asymmetric Domino Michael/Henry Reaction in Aqueous Media. Synth Catal 2011, 353, 2905. <http://dx.doi.org/10.1002/adsc.201100395>
  • Rahmatpour Ali: ZrOCl2·8H2O as a highly efficient, eco-friendly and recyclable Lewis acid catalyst for one-pot synthesis of N-substituted pyrroles under solvent-free conditions at room temperature. Appl Organometal Chem 2011, 25, 585. <http://dx.doi.org/10.1002/aoc.1806>
  • Silva Milene L., Figueiredo Ana P., Cardoso Abiney L., Natalino Ricardo, Silva Márcio J.: Effect of Water on the Ethanolysis of Waste Cooking Soybean Oil Using a Tin(II) Chloride Catalyst. J Am Oil Chem Soc 2011, 88, 1431. <http://dx.doi.org/10.1007/s11746-011-1794-z>
  • Spindler Xanthe, Shimmon Ronald, Roux Claude, Lennard Chris: The effect of zinc chloride, humidity and the substrate on the reaction of 1,2-indanedione–zinc with amino acids in latent fingermark secretions. Forensic Sci Int 2011, 212, 150. <http://dx.doi.org/10.1016/j.forsciint.2011.06.005>
  • Penhoat Maël, Barbry Didier, Rolando Christian: Direct asymmetric aldol reaction co-catalyzed by l-proline and group 12 elements Lewis acids in the presence of water. Tetrahedron Letters 2011, 52, 159. <http://dx.doi.org/10.1016/j.tetlet.2010.11.014>
  • Kumar Atul, Gupta Maneesh Kumar, Kumar Mukesh: An efficient non-ionic surfactant catalyzed multicomponent synthesis of novel benzylamino coumarin derivative via Mannich type reaction in aqueous media. Tetrahetron Lett 2011, 52, 4521. <http://dx.doi.org/10.1016/j.tetlet.2011.06.040>
  • Firouzabadi Habib, Iranpoor Nasser, Gholinejad Mohammad: 2-Aminophenyl diphenylphosphinite as an easily accessible ligand for heterogeneous palladium-catalyzed Suzuki–Miyaura reaction in water in the absence of any organic co-solvent. J Organomet Chem 2010, 695, 2093. <http://dx.doi.org/10.1016/j.jorganchem.2010.05.016>
  • Kumar Anil, Rao M. Sudershan, Kameshwara Rao V.: Cerium Triflate: An Efficient and Recyclable Catalyst for Chemoselective Thioacetalization of Carbonyl Compounds under Solvent-Free Conditions. Aust J Chem 2010, 63, 135. <http://dx.doi.org/10.1071/CH09296>
  • Evanno Laurent, Ormala Joel, Pihko Petri M.: A Highly Enantioselective Access to Tetrahydroisoquinoline and β-Carboline Alkaloids with Simple Noyori-Type Catalysts in Aqueous Media. Chem Eur J 2009, 15, 12963. <http://dx.doi.org/10.1002/chem.200902289>
  • Ghesti Grace Ferreira, Macedo Julio Lemos de, Parente Vicente Cavalcanti Ibiapina, Dias José Alves, Dias Sílvia Cláudia Loureiro: Synthesis, characterization and reactivity of Lewis acid/surfactant cerium trisdodecylsulfate catalyst for transesterification and esterification reactions. CATAL A GENERAL 2009, 355, 139. <http://dx.doi.org/10.1016/j.apcata.2008.12.008>
  • Arasa Mercé, Ramis Xavier, Salla Josep Maria, Ferrando Francesc, Serra Angels, Mantecón Ana: Study on the effect of rare earth metal triflates as initiators in the cationic curing of DGEBA/γ-valerolactone mixtures and characterization of the thermosets obtained. Euro Poly J 2009, 45, 1282. <http://dx.doi.org/10.1016/j.eurpolymj.2008.11.026>
  • Shiri Morteza, Zolfigol Mohammad Ali: Surfactant-type catalysts in organic reactions. Tetrahedron 2009, 65, 587. <http://dx.doi.org/10.1016/j.tet.2008.09.085>
  • Oliver Scott R. J.: Cationic inorganic materials for anionic pollutant trapping and catalysis. Chem Soc Rev 2009, 38, 1868. <http://dx.doi.org/10.1039/b710339p>
  • Kleiner Christian M., Horst Luise, Würtele Christian, Wende Raffael, Schreiner Peter R.: Isolation of the key intermediates in the catalyst-free conversion of oxiranes to thiiranes in water at ambient temperature. Org Biomol Chem 2009, 7, 1397. <http://dx.doi.org/10.1039/b820232j>
  • Qiu Renhua, Xu Xinhua, Li Yinhui, Zhang Guoping, Shao Lingling, An Delie, Yin Shuangfeng: Synthesis and structure of air-stable Lewis acidic binuclear complex of zirconocene pentafluorophenylsulfonate and its catalytic application in the allylation of carbonyl compounds with tetraallyltin. Chem Commun 2009, 1679. <http://dx.doi.org/10.1039/b821366f>
  • Mu Bing, Li Tiesheng, Li Jingya, Wu Yangjie: The highly efficient Suzuki–Miyaura cross-coupling reaction using cyclopalladated N-alkylferrocenylimine as a catalyst in aqueous medium at room temperature under ambient atmosphere. J Organomet Chem 2008, 693, 1243. <http://dx.doi.org/10.1016/j.jorganchem.2008.01.012>
  • Marquet Nicolas, Grunova Ekaterina, Kirillov Evgueni, Bouyahyi Miloud, Thomas Christophe M., Carpentier Jean-François: Convenient synthesis of mono- and di-β-hydroxy-β-bis(trifluoromethyl)-(di)imines from β-hydroxy-β-bis(trifluoromethyl)-ketones and (di)amines. Tetrahedron 2008, 64, 75. <http://dx.doi.org/10.1016/j.tet.2007.10.096>
  • Mlynarski Jacek, Paradowska Joanna: Catalytic asymmetric aldol reactions in aqueous media. Chem Soc Rev 2008, 37, 1502. <http://dx.doi.org/10.1039/b710577k>
  • Heravi Majid M., Taheri Shima, Bakhtiari Khadijeh, Oskooie Hossein A.: On Water: A practical and efficient synthesis of quinoxaline derivatives catalyzed by CuSO4·5H2O. Catal Commun 2007, 8, 211. <http://dx.doi.org/10.1016/j.catcom.2006.06.013>
  • Witayakran Suteera, Gelbaum Leslie, Ragauskas Arthur J.: Cascade synthesis of benzofuran derivatives via laccase oxidation–Michael addition. Tetrahedron 2007, 63, 10958. <http://dx.doi.org/10.1016/j.tet.2007.08.066>
  • Kouznetsov Vladimir V., Bohórquez Arnold R. Romero, Stashenko Elena E.: Three-component imino Diels–Alder reaction with essential oil and seeds of anise: generation of new tetrahydroquinolines. Tetrahetron Lett 2007, 48, 8855. <http://dx.doi.org/10.1016/j.tetlet.2007.10.063>
  • Ballini Roberto, Barboni Luciano, Fringuelli Francesco, Palmieri Alessandro, Pizzo Ferdinando, Vaccaro Luigi: Recent developments on the chemistry of aliphatic nitro compounds under aqueous medium. Green Chem 2007, 9, 823. <http://dx.doi.org/10.1039/b702334k>
  • Rix Diane, Clavier Hervé, Coutard Yann, Gulajski Lukasz, Grela Karol, Mauduit Marc: Activated pyridinium-tagged ruthenium complexes as efficient catalysts for ring-closing metathesis. J Organomet Chem 2006, 691, 5397. <http://dx.doi.org/10.1016/j.jorganchem.2006.07.042>
  • Li Jin-Heng, Hu Xi-Chao, Liang Yun, Xie Ye-Xiang: PEG-400 promoted Pd(OAc)2/DABCO-catalyzed cross-coupling reactions in aqueous media. Tetrahedron 2006, 62, 31. <http://dx.doi.org/10.1016/j.tet.2005.09.138>
  • Larini Paolo, Guarna Antonio, Occhiato Ernesto G.: The Lewis Acid-Catalyzed Nazarov Reaction of 2-(N-Methoxycarbonylamino)-1,4-pentadien-3-ones. Org Lett 2006, 8, 781. <http://dx.doi.org/10.1021/ol053071h>
  • Mennecke Klaas, Kirschning Andreas, Grela Karol, Michrowska Anna, Gu?ajski ?ukasz, Kaczmarska Zuzanna: A green catalyst for green chemistry: Synthesis and application of an olefin metathesis catalyst bearing a quaternary ammonium group. Green Chem 2006, 8, 685. <http://dx.doi.org/10.1039/b605138c>
  • Dwars Torsten, Paetzold Eckhard, Oehme Günther: Reaktionen in micellaren Systemen. Angew Chem 2005, 117, 7338. <http://dx.doi.org/10.1002/ange.200501365>
  • Dwars Torsten, Paetzold Eckhard, Oehme Günther: Reactions in Micellar Systems. Angew Chem Int Ed 2005, 44, 7174. <http://dx.doi.org/10.1002/anie.200501365>
  • Zhang Ji, Blazecka Peter G., Angell Paul, Lovdahl Mark, Curran Timothy T.: Indium (III) mediated Markovnikov addition of malonates and β-ketoesters to terminal alkynes and the formation of Knoevenagel condensation products. Tetrahedron 2005, 61, 7807. <http://dx.doi.org/10.1016/j.tet.2005.05.065>
  • Zhang Zhan-Hui, Yin Liang, Li Yi, Wang Yong-Mei: A practical and efficient procedure for the cleavage of acylals to aldehydes catalyzed by indium tribromide in water. Tetrahetron Lett 2005, 46, 889. <http://dx.doi.org/10.1016/j.tetlet.2004.11.161>
  • Mahalingam A. K., Wu Xiongyu, Wan Yiqian, Alterman Mathias: Scandium Triflate as an Efficient and Recyclable Catalyst for the Deprotection of Tert‐Butyl Aryl Sulfonamides. Synth Common 2005, 35, 417. <http://dx.doi.org/10.1081/SCC-200048949>
  • Beckman Eric J: Supercritical and near-critical CO2 in green chemical synthesis and processing. J Sup Fluids 2004, 28, 121. <http://dx.doi.org/10.1016/S0896-8446(03)00029-9>
  • Sumino Yukihito, Harato Nami, Tomisaka Yuri, Ogawa Akiya: A novel photoinduced reduction system of low-valent samarium species: reduction of organic halides and chalcogenides, and its application to carbonylation with carbon monoxide. Tetrahedron 2003, 59, 10499. <http://dx.doi.org/10.1016/j.tet.2003.08.070>
  • Fu Nan-Yan, Yuan Yao-Feng, Cao Zhong, Wang Shan-Wei, Wang Ji-Tao, Peppe Clovis: Indium(III) bromide-catalyzed preparation of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction. Tetrahedron 2002, 58, 4801. <http://dx.doi.org/10.1016/S0040-4020(02)00455-6>
  • Kawada Atsushi, Takeda Shigemitsu, Yamashita Kazumi, Abe Hitoshi, Harayama Takashi: Scandium(III) Trifluoromethanesulfonate Catalyzed Aromatic Nitration with Inorganic Nitrates and Acetic Anhydride. Chem Pharm Bull 2002, 50, 1060. <http://dx.doi.org/10.1248/cpb.50.1060>
  • Kobayashi Shu, Manabe Kei: ChemInform Abstract: Green Lewis Acid Catalysis in Organic Synthesis. ChemInform 2001, 32, no. <http://dx.doi.org/10.1002/chin.200113267>