Dehydration Reactions in Water. Brønsted Acid−Surfactant-Combined Catalyst for Ester, Ether, Thioether, and Dithioacetal Formation in Water
Abstract
Dehydration reactions in water have been realized by a surfactant-type catalyst, dodecylbenzenesulfonic acid (DBSA). These reactions include dehydrative esterification, etherification, thioetherification, and dithioacetalization. In these reactions, DBSA and substrates form emulsion droplets whose interior is hydrophobic enough to exclude water molecules generated during the reactions. Detailed studies on the esterification revealed that the yields of esters were affected by temperature, amounts of DBSA used, and the substrates. Esters were obtained in high yields for highly hydrophobic substrates. On the basis of the difference in hydrophobicity of the substrates, unique selective esterification and etherification in water were attained. Furthermore, chemospecific, three-component reactions under DBSA-catalyzed conditions were also found to proceed smoothly. This work not only may lead to environmentally benign systems but also will provide a new aspect of organic chemistry in water.
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Kobayashi developed a unique catalytic system using a surfactant-like acid, DBSA, to mediate the emulsion polycondensation of aliphatic carboxylic acids and alcohols in water.
“Kobayashi developed a unique catalytic system [250][251][252] using a surfactant-like acid, such as dodecylbenzenesulfonic acid (DBSA), to mediate the emulsion polycondensation of aliphatic carboxylic acids and alcohols in water.”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [251]
Cites
Green Chemistry: Theory and Practice
Anastas, P. T., & Warner, J. C. (1998) · Medical Entomology and Zoology · Cited by 8,599 · see citing works
Comprehensive supramolecular chemistry
(1997) · Choice Reviews Online · doi:10.5860/choice.34-5097 · Cited by 6,484 · see citing works
Comprehensive organic synthesis
Knochel, P., & Molander, G. A. (2014) · Elsevier eBooks · Cited by 6,229 · see citing works
Protective Groups in Organic Synthesis
Greene, T. W., & Wuts, P. G. M. (1999) · Wiley eBooks · doi:10.1002/0471220574 · Cited by 5,677 · see citing works
Hydrophobic acceleration of Diels-Alder reactions
Rideout, D. C., & Breslow, R. (1980) · Journal of the American Chemical Society · doi:10.1021/ja00546a048 · Cited by 1,548 · see citing works
Organic reactions in aqueous media
(1998) · Choice Reviews Online · doi:10.5860/choice.35-3311 · Cited by 1,264 · see citing works
Comprehensive Organic Transformations
(2017) · Wiley eBooks · doi:10.1002/9781118662083 · Cited by 1,118 · see citing works
Octanol-Water Partition Coefficients of Simple Organic Compounds
Sangster, J. M. (1989) · Journal of Physical and Chemical Reference Data · doi:10.1063/1.555833 · Cited by 856 · see citing works
A General Theory of the Mechanism of Emulsion Polymerization 1
Harkins, W. D. (1947) · Journal of the American Chemical Society · doi:10.1021/ja01198a053 · Cited by 786 · see citing works
Synthetic pathways and processes in green chemistry. Introductory overview
Tundo, P., Anastas, P. T., Black, D. S., et al. (2000) · Pure and Applied Chemistry · doi:10.1351/pac200072071207 · Cited by 494 · see citing works
3,4,5-Trifluorobenzeneboronic Acid as an Extremely Active Amidation Catalyst
Ishihara, K., Ohara, S., & Yamamoto, H. (1996) · The Journal of Organic Chemistry · doi:10.1021/jo9606564 · Cited by 490 · see citing works
Yamakawa, M., Yamada, I., & Noyori, R. (2001) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20010803)40:15 · Cited by 403 · see citing works
Otera, J., DAN‐OH, N., & Nozaki, H. (1991) · The Journal of Organic Chemistry · doi:10.1021/jo00018a019 · Cited by 356 · see citing works
Direct Condensation of Carboxylic Acids with Alcohols Catalyzed by Hafnium(IV) Salts
Ishihara, K., Ohara, S., & Yamamoto, H. (2000) · Science · doi:10.1126/science.290.5494.1140 · Cited by 337 · see citing works
Surfactants And Polymers In Aqueous Solutions
Shea, J. J. (1998) · IEEE Electrical Insulation Magazine · doi:10.1109/mei.1998.714652 · Cited by 329 · see citing works
Manabe, K., Mori, Y., Wakabayashi, T., Nagayama, S., & Kobayashi, S. (2000) · Journal of the American Chemical Society · doi:10.1021/ja001420r · Cited by 288 · see citing works
Self-citationManabe, K., Sun, X.-M., & Kobayashi, S. (2001) · Journal of the American Chemical Society · doi:10.1021/ja016338q · Cited by 215 · see citing works
Self-citation(1961) · Elsevier eBooks · doi:10.1016/c2013-0-08067-x · Cited by 210 · see citing works
Manabe, K., & Kobayashi, S. (1999) · Organic Letters · doi:10.1021/ol991113u · Cited by 207 · see citing works
Self-citationNiemeyer, C. M., & Ceyhan, B. (2001) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20011001)40:19 · Cited by 197 · see citing works
Facile synthesis of α-amino phosphonates in water using a Lewis acid–surfactant-combined catalyst
Manabe, K., & Kobayashi, S. (2000) · Chemical Communications · doi:10.1039/b000319k · Cited by 186 · see citing works
Self-citationManabe, K., Mori, Y., & Kobayashi, S. (2001) · Tetrahedron · doi:10.1016/s0040-4020(01)00081-3 · Cited by 178 · see citing works
Self-citationOtto, S., Engberts, J. B. F. N., & Kwak, J. C. T. (1998) · Journal of the American Chemical Society · doi:10.1021/ja9816537 · Cited by 176 · see citing works
Kobayashi, S., Wakabayashi, T., Nagayama, S., & Oyamada, H. (1997) · Tetrahedron Letters · doi:10.1016/s0040-4039(97)00854-x · Cited by 160 · see citing works
Self-citationSynthesis of various kinds of esters by four microbial lipases
Okumura, S., Mieko, I., & Tsujisaka, Y. (1979) · Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism · doi:10.1016/0005-2760(79)90141-3 · Cited by 154 · see citing works
Kobayashi, S., & Wakabayashi, T. (1998) · Tetrahedron Letters · doi:10.1016/s0040-4039(98)01081-8 · Cited by 144 · see citing works
Self-citationManabe, K., Aoyama, N., & Kobayashi, S. (2001) · Advanced Synthesis & Catalysis · doi:10.1002/1615-4169(20010226)343:2 · Cited by 125 · see citing works
Self-citationTrost, B. M., & Murayama, E. (1981) · Journal of the American Chemical Society · doi:10.1021/ja00411a058 · Cited by 119 · see citing works
Michael reactions in water using Lewis acid–surfactant-combined catalysts
Mori, Y., Kakumoto, K., Manabe, K., & Kobayashi, S. (2000) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)00319-1 · Cited by 116 · see citing works
Self-citationManabe, K., Mori, Y., & Kobayashi, S. (1999) · Synlett · doi:10.1055/s-1999-2871 · Cited by 86 · see citing works
Self-citationCatalytic asymmetric aldol reactions in water
Kobayashi, S., Mori, Y., Nagayama, S., et al. (1999) · Green Chemistry · doi:10.1039/a904439f · Cited by 85 · see citing works
Self-citationAkiyama, T., Takaya, J., & Kagoshima, H. (1999) · Tetrahedron Letters · doi:10.1016/s0040-4039(99)01630-5 · Cited by 71 · see citing works
Manabe, K., & Kobayashi, S. (1999) · Tetrahedron Letters · doi:10.1016/s0040-4039(99)00606-1 · Cited by 70 · see citing works
Self-citationEffects of Lewis acid-surfactant-combined catalysts on aldol and Diels-Alder reactions in water
Manabe, K., Mori, Y., & Kobayashi, S. (1999) · Tetrahedron · doi:10.1016/s0040-4020(99)00642-0 · Cited by 67 · see citing works
Self-citationAkiyama, T., Takaya, J., & Kagoshima, H. (1999) · Synlett · doi:10.1055/s-1999-2872 · Cited by 67 · see citing works
Izumi, J., Shiina, I., & Mukaiyama, T. (1995) · Chemistry Letters · doi:10.1246/cl.1995.141 · Cited by 65 · see citing works
Sharma, & Mahalingam (1999) · The Journal of Organic Chemistry · doi:10.1021/jo990563x · Cited by 65 · see citing works
Efficient Catalysis of a Diels−Alder Reaction by Metallo-Vesicles in Aqueous Solution
Rispens, T. T., & Engberts, J. B. F. N. (2001) · Organic Letters · doi:10.1021/ol015611q · Cited by 63 · see citing works
tert-Butyl group as thiol protection in peptide synthesis
Pastuszak, J. J., & CHIMIAK, A. (1981) · The Journal of Organic Chemistry · doi:10.1021/jo00322a024 · Cited by 62 · see citing works
Enzymatic synthesis of functional oligomers, 1 lipase catalyzed polymerization of hydroxy acids
Matsumura, S., & Takahashi, J. A. (1986) · Die Makromolekulare Chemie Rapid Communications · doi:10.1002/marc.1986.030070609 · Cited by 60 · see citing works
Organic reactions in excess water catalyzed by solid acids
Okuhara, T., Kimura, M., Kawai, T., et al. (1998) · Catalysis Today · doi:10.1016/s0920-5861(98)00251-x · Cited by 60 · see citing works
Dehydration Polymerization in Aqueous Medium Catalyzed by Lipase
Kobayashi, S., Uyama, H., Suda, S., & Namekawa, S. (1997) · Chemistry Letters · doi:10.1246/cl.1997.105 · Cited by 56 · see citing works
Self-citationUmpoled synthons: A survey of sources and uses in synthesis
(1987) · European Journal of Medicinal Chemistry · doi:10.1016/0223-5234(87)90283-2 · Cited by 54 · see citing works
Lewis‐acid catalysis of carbon carbon bond forming reactions in water
Engberts, J. B. F. N., Feringa, B. L., Keller, E., & Otto, S. (1996) · Recueil des Travaux Chimiques des Pays-Bas · doi:10.1002/recl.19961151103 · Cited by 54 · see citing works
Manabe, K., Mori, Y., Nagayama, S., et al. (1999) · Inorganica Chimica Acta · doi:10.1016/s0020-1693(99)00354-0 · Cited by 53 · see citing works
Self-citationA CONVENIENT METHOD FOR THE PREPARATION OF γ-KETOSULFIDES FROM THIOACETALS
Ohshima, M., Murakami, M., & Mukaiyama, T. (1985) · Chemistry Letters · doi:10.1246/cl.1985.1871 · Cited by 50 · see citing works
Dehydration polycondensation in water for synthesis of polyesters by lipase catalyst
Suda, S., Uyama, H., & Kobayashi, S. (1999) · Proceedings of the Japan Academy Series B · doi:10.2183/pjab.75.201 · Cited by 48 · see citing works
Self-citationCeschi, M. A., Felix, L. D. A., & Peppe, C. (2000) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)01741-x · Cited by 47 · see citing works
Manabe, K., & Kobayashi, S. (1999) · Synlett · doi:10.1055/s-1999-2685 · Cited by 41 · see citing works
Self-citationStorck, S., Maier, W. F., Salvado, I. M. M., Ferreira, J. M. F., Guhl, D., Souverijns, W., & Martens, J. A. (1997) · Journal of Catalysis · doi:10.1006/jcat.1997.1847 · Cited by 36 · see citing works
Masaki, Y., Tanaka, N., & Miura, T. (1997) · Chemistry Letters · doi:10.1246/cl.1997.55 · Cited by 33 · see citing works
Gallium Chloride-Mediated Allylation of Dithioacetals with Allylstannanes
Saigo, K., Hashimoto, Y., Kihara, N., et al. (1990) · Chemistry Letters · doi:10.1246/cl.1990.1097 · Cited by 25 · see citing works
Lewis Acid Mediated α-Thioalkylation of Ketones
Reetz, M. T., & Giannis, A. (1981) · Synthetic Communications · doi:10.1080/00397918108063611 · Cited by 25 · see citing works
Direct polyesterifcation in aqueous emulsion
Baile, M., Chou, Y. J., & Saam, J. C. (1990) · Polymer Bulletin · doi:10.1007/bf01032438 · Cited by 21 · see citing works
Zhang, G. (1999) · Synthetic Communications · doi:10.1080/00397919908085809 · Cited by 21 · see citing works
Synthese schwefelhaltiger Carbamazepin‐Derivate
Scholl, T., & Roth, H. J. (1985) · Archiv der Pharmazie · doi:10.1002/ardp.19853180710 · Cited by 3 · see citing works
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Zhang, X., Fevre, M., Jones, G. O., & Waymouth, R. M. (2018) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00329 · Cited by 936 · see citing works
The quest for sustainable polyesters – insights into the future
Vilela, C., Sousa, A. F., Fonseca, A. C., Serra, A. C., Coelho, J. F. J., Freire, C. S. R., & Silvestre, A. J. D. (2014) · Polym. Chem. · doi:10.1039/c3py01213a · Cited by 527 · see citing works
Takasu, A., Takemoto, A., & Hirabayashi, T. (2006) · Biomacromolecules · doi:10.1021/bm050485p · Cited by 60 · see citing works
Synthesis of aliphatic suberin-like polyesters by ecofriendly catalytic systems
Sousa, A. F., Silvestre, A. J. D., Gandini, A., & Neto, C. P. (2012) · High Performance Polymers · doi:10.1177/0954008311431114 · Cited by 29 · see citing works
- Authors
- Manabe, K., Iimura, S., Sun, X.-M., & Kobayashi, S.
- Affiliations
- The University of Tokyo (JP)
- Corresponding author
- Kobayashi, Shū
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-09-13
- Volume
- 124
- Issue
- 40
- Pages
- 11971-11978
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1982368556
- Cited by
- 401
- References
- 56
- Citations by year
- 2026: 8 · 2025: 15 · 2024: 12 · 2023: 13 · 2022: 15 · 2021: 15 · 2020: 18 · 2019: 12 · 2018: 20 · 2017: 20 · 2016: 11 · 2015: 19 · 2014: 27 · 2013: 36 · 2012: 23
- FWCI
- 8.36
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Reactions
- Physical Sciences › Chemistry › Organic Chemistry › Multicomponent Synthesis of Heterocycles
- Physical Sciences › Chemistry › Organic Chemistry › Surfactants and Colloidal Systems
- Keywords
- dodecylbenzenesulfonic acid, Brønsted acid catalysis, thioetherification, emulsion droplets, hydrophobicity, selective esterification, three-component reaction, green chemistry
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