The DOI matches its Crossref record; 63 of the 63 references it cites were found in a registry or an index.
Catalytic Reductive Transformations of Carboxylic and Carbonic Acid Derivatives Using Molecular Hydrogen
Abstract
A comprehensive overview on homogeneous catalytic hydrogenation of carboxylic acids and its derivatives as well as carbonic acid derivatives with transition metal-based molecular catalysts is described. Despite the tremendous potential in the hydrogenation of these less electrophilic carbonyl compounds using molecular hydrogen in synthetic organic chemistry, their reduction still relies mostly on the stoichiometric use of metal hydride reagents, such as LiAlH 4, NaBH 4, and their derivatives. For the past decade, a significant and rapid progress in particularly ester hydrogenation has been achieved by utilization of conceptually new bifunctional molecular catalysts originating from the metal–ligand cooperation effects. The bifunctional-catalyst-promoted hydrogenation using molecular hydrogen is now realized to be a practical tool in synthetic organic chemistry in both academia and industry. The industrial outlook for the present hydrogenation is bright because of its operational simplicity, scope, economic viability, and growing awareness of the need for green chemistry.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering
Huber, G. W., Iborra, S., & Corma, A. (2006) · Chemical Reviews · doi:10.1021/cr068360d · Cited by 7,664
Chemical Routes for the Transformation of Biomass into Chemicals
Corma, A., Iborra, S., & Velty, A. (2007) · Chemical Reviews · doi:10.1021/cr050989d · Cited by 5,970
New Chiral Phosphorus Ligands for Enantioselective Hydrogenation
Tang, W., & Zhang, X. (2003) · Chemical Reviews · doi:10.1021/cr020049i · Cited by 2,570
Production of Liquid Alkanes by Aqueous-Phase Processing of Biomass-Derived Carbohydrates
Huber, G. W., Chheda, J. N., Barrett, C. J., & Dumesic, J. A. (2005) · Science · doi:10.1126/science.1111166 · Cited by 1,678
Clapham, S. E., Hadzovic, A., & Morris, R. H. (2004) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2004.04.007 · Cited by 1,316
Ikariya, T., & Blacker, A. J. (2007) · Accounts of Chemical Research · doi:10.1021/ar700134q · Cited by 1,185
Self-citationGunanathan, C., & Milstein, D. (2011) · Accounts of Chemical Research · doi:10.1021/ar2000265 · Cited by 1,078
Kubas, G. J. (2007) · Chemical Reviews · doi:10.1021/cr050197j · Cited by 1,003
γ-Valerolactone—a sustainable liquid for energy and carbon-based chemicals
Horváth, I. T., Mehdi, H., Fábos, V., Boda, L., & Mika, L. T. (2008) · Green Chem. · doi:10.1039/b712863k · Cited by 992
Metal Dihydrogen and σ-Bond Complexes: Structure Theory and Reactivity
Kubas, G. J. (2001) · Springer eBooks · doi:10.1007/b113929 · Cited by 738
Balaraman, E., Gunanathan, C., Zhang, J., Shimon, L. J. W., & Milstein, D. (2011) · Nature Chemistry · doi:10.1038/nchem.1089 · Cited by 655
Geilen, F. M. A., Engendahl, B., Harwardt, A., Marquardt, W., Klankermayer, J., & Leitner, W. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.201002060 · Cited by 618
Cascade Catalysis for the Homogeneous Hydrogenation of CO2to Methanol
Huff, C. A., & Sanford, M. S. (2011) · Journal of the American Chemical Society · doi:10.1021/ja208760j · Cited by 587
Efficient Homogeneous Catalytic Hydrogenation of Esters to Alcohols
Zhang, J., Leitus, G., Ben‐David, Y., & Milstein, D. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200503771 · Cited by 566
Mehdi, H., Fábos, V., Tuba, R., Bodor, A., Mika, L. T., & Horváth, I. T. (2008) · Topics in Catalysis · doi:10.1007/s11244-008-9047-6 · Cited by 462
Direct Hydrogenation of Amides to Alcohols and Amines under Mild Conditions
Balaraman, E., Gnanaprakasam, B., Shimon, L. J. W., & Milstein, D. (2010) · Journal of the American Chemical Society · doi:10.1021/ja1080019 · Cited by 435
Enantioselective catalysis in fine chemicals production
Blaser, H.-U. (2003) · Chemical Communications · doi:10.1039/b209968n · Cited by 378
Deng, L., Li, J., Lai, D., Fu, Y., & Guo, Q. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200902281 · Cited by 366
Catalytic upgrading of levulinic acid to 5-nonanone
Serrano-Ruiz, J. C., Wang, D., & Dumesic, J. A. (2010) · Green Chemistry · doi:10.1039/b923907c · Cited by 362
Developments in Asymmetric Hydrogenation from an Industrial Perspective
Shimizu, H., Nagasaki, I., Matsumura, K., Sayo, N., & Saito, T. (2007) · Accounts of Chemical Research · doi:10.1021/ar700101x · Cited by 310
Hydrogen vehicles: Fuel of the future?
Tollefson, J. (2010) · Nature · doi:10.1038/4641262a · Cited by 306
Käß, M., Friedrich, A., Drees, M., & Schneider, S. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200805108 · Cited by 306
From Esters to Alcohols and Back with Ruthenium and Osmium Catalysts
Spasyuk, D., Smith, S., & Gusev, D. G. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201108956 · Cited by 296
Saudan, L. A., Saudan, C. M., Debieux, C., & Wyss, P. (2007) · Angewandte Chemie International Edition · doi:10.1002/anie.200701015 · Cited by 251
Geilen, F. M. A., Engendahl, B., Hölscher, M., Klankermayer, J., & Leitner, W. (2011) · Journal of the American Chemical Society · doi:10.1021/ja2034377 · Cited by 249
The synthesis of amines by the homogeneous hydrogenation of secondary and primary amides
Núñez Magro, A. A., Eastham, G. R., & Cole-Hamilton, D. J. (2007) · Chemical Communications · doi:10.1039/b706635j · Cited by 238
The Catalytic Hydrogenolysis of Esters to Alcohols
Turek, T., Trimm, D. L., & Cant, N. W. (1994) · Catalysis Reviews · doi:10.1080/01614949408013931 · Cited by 231
Schlaf, M. (2006) · Dalton Trans. · doi:10.1039/b608007c · Cited by 224
Grey, R. A., Pez, G. P., & Wallo, A. (1981) · Journal of the American Chemical Society · doi:10.1021/ja00415a022 · Cited by 224
Ito, M., Ootsuka, T., Watari, R., Shiibashi, A., Himizu, A., & Ikariya, T. (2011) · Journal of the American Chemical Society · doi:10.1021/ja1117254 · Cited by 209
Self-citationLong-Chain Linear C 19 and C 23 Monomers and Polycondensates from Unsaturated Fatty Acid Esters
Stempfle, F., Quinzler, D., Heckler, I., & Mecking, S. (2011) · Macromolecules · doi:10.1021/ma200627e · Cited by 203
Unprecedented Catalytic Hydrogenation of Urea Derivatives to Amines and Methanol
Balaraman, E., Ben‐David, Y., & Milstein, D. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201106612 · Cited by 202
Stereoselective Anhydride Openings
Atodiresei, I., Schiffers, I., & Bolm, C. (2007) · Chemical Reviews · doi:10.1021/cr068369f · Cited by 197
Unlocking the Potential of Asymmetric Hydrogenation at Merck
Shultz, C. S., & Krska, S. W. (2007) · Accounts of Chemical Research · doi:10.1021/ar700141v · Cited by 195
Homogeneous ruthenium catalyzed hydrogenation of esters to alcohols‡
Teunissen, H. T. (1998) · Chemical Communications · doi:10.1039/a801807c · Cited by 159
Ruthenium catalysed hydrogenation of dimethyl oxalate to ethylene glycol
Teunissen, H. T., & Elsevier, C. J. (1997) · Chemical Communications · doi:10.1039/a700862g · Cited by 148
A Highly Active Catalyst for the Hydrogenation of Amides to Alcohols and Amines
John, J. M., & Bergens, S. H. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201103137 · Cited by 145
Chemistry of Concerto Molecular Catalysis Based on the Metal/NH Bifunctionality
Ikariya, T. (2010) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.20100249 · Cited by 130
Self-citationO, W. W. N., Lough, A. J., & Morris, R. H. (2010) · Chemical Communications · doi:10.1039/c0cc02664f · Cited by 130
Efficient hydrogenation of biomass-derived cyclic di-esters to 1,2-diols
Balaraman, E., Fogler, E., & Milstein, D. (2011) · Chemical Communications · doi:10.1039/c1cc15778g · Cited by 125
Bianchi, M., Menchi, G., Francalanci, F., Piacenti, F., Matteoli, U., Frediani, P., & BOTTEGHI, C. (1980) · Journal of Organometallic Chemistry · doi:10.1016/s0022-328x(00)83702-x · Cited by 121
Suitable ligands for homogeneous ruthenium-catalyzed hydrogenolysis of esters
van Engelen, M. C., Teunissen, H. T., de Vries, J. G., et al. (2003) · Journal of Molecular Catalysis A Chemical · doi:10.1016/s1381-1169(03)00427-8 · Cited by 105
Tang, Y., Yu, W., Mo, L., Lou, H., & Zheng, X. (2008) · Energy & Fuels · doi:10.1021/ef800148q · Cited by 103
Production of fatty alcohols from fatty acids
Voeste, T., & Buchold, H. (1984) · Journal of the American Oil Chemists Society · doi:10.1007/bf02678794 · Cited by 100
Selective Hydrogenation of Amides using Ruthenium/ Molybdenum Catalysts
Beamson, G., Papworth, A. J., Philipps, C., Smith, A. M., II, & Whyman, R. (2010) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.200900824 · Cited by 81
Rieke, R. D., Thakur, D. S., Roberts, B. D., & White, G. T. (1997) · Journal of the American Oil Chemists Society · doi:10.1007/s11746-997-0088-y · Cited by 79
Homogeneous catalytic hydrogenation dicarboxylic acid esters. II
Matteoli, U., Menchi, G., Bianchi, M., et al. (1986) · Journal of Organometallic Chemistry · doi:10.1016/0022-328x(86)82019-8 · Cited by 73
Structure and catalytic activity of phosphine-substituted ruthenium carbonyl carboxylates
Matteoli, U., Menchi, G., Bianchi, M., Piacenti, F., Ianelli, S., & Nardelli, M. (1995) · Journal of Organometallic Chemistry · doi:10.1016/0022-328x(95)05518-t · Cited by 65
A Novel Production of γ-Butyrolactone Catalyzed by Ruthenium Complexes
Hara, Y., Kusaka, H., Inagaki, H., Takahashi, K., & Wada, K. (2000) · Journal of Catalysis · doi:10.1006/jcat.2000.2945 · Cited by 65
Yang, X. (2012) · ACS Catalysis · doi:10.1021/cs3000683 · Cited by 63
Homogeneous catalytic hydrogenation of dicarboxylic acid esters
Matteoli, U., Blanchi, M., Menchi, G., et al. (1984) · Journal of Molecular Catalysis · doi:10.1016/0304-5102(84)80075-9 · Cited by 60
Dixneuf, P. H. (2011) · Nature Chemistry · doi:10.1038/nchem.1103 · Cited by 59
Isotopomeric diols by “one-pot” Ru-catalyzed homogeneous hydrogenation of dicarboxylic acids
Rosi, L., Frediani, M., & Frediani, P. (2010) · Journal of Organometallic Chemistry · doi:10.1016/j.jorganchem.2010.02.015 · Cited by 56
Ruthenium catalyzed hydrogenation of methyl phenylacetate under low hydrogen pressure
Nomura, K., Ogura, H., & Imanishi, Y. (2002) · Journal of Molecular Catalysis A Chemical · doi:10.1016/s1381-1169(01)00281-3 · Cited by 52
Matteoli, U., Menchi, G., Bianchi, M., et al. (1991) · Journal of Molecular Catalysis · doi:10.1016/0304-5102(91)85135-o · Cited by 52
Tang, Y., Miao, S., Shanks, B. H., & Zheng, X. (2010) · Applied Catalysis A General · doi:10.1016/j.apcata.2010.01.015 · Cited by 49
A tripodal sulfur ligand for the selective ruthenium-catalysed hydrogenation of dimethyl oxalate
Boardman, B., Hanton, M. J., van Rensburg, H., et al. (2006) · Chemical Communications · doi:10.1039/b601216g · Cited by 43
Liquid-phase hydrogenation of car☐ylic acid on supported bimetallic Ru Sn-Alumina catalysts
Tahara, K., Nagahara, E., Itoi, Y., Nishiyama, S., Tsuruya, S., & Masai, M. (1997) · Applied Catalysis A General · doi:10.1016/s0926-860x(96)00361-4 · Cited by 40
Lyons, J. E. (1975) · Journal of the Chemical Society Chemical Communications · doi:10.1039/c39750000412 · Cited by 37
Highly regioselective reduction of unsymmetrical cyclic carboxylic acid anhydrides to γ-lactones
Morand, P. F., & Kayser, M. M. (1976) · Journal of the Chemical Society Chemical Communications · doi:10.1039/c39760000314 · Cited by 33
Ikariya, T., Osakada, K., Ishii, Y., Osawa, S., Saburi, M., & Yoshikawa, S. (1984) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.57.897 · Cited by 24
Self-citationRegio-selective reaction of cyclic anhydride with RuH2 (PPh3)4
Ikariya, T., Osakada, K., & Yoshikawa, S. (1978) · Tetrahedron Letters · doi:10.1016/s0040-4039(01)95049-x · Cited by 12
Self-citationSodium Sulfide Catalyzed Isomerization of Itaconic Anhydride to Citraconic Anhydride
Schneider, K. J., & Williams, J. D. (2011) · Current Organic Chemistry · doi:10.2174/138527211796378433 · Cited by 6
Cited by
Computational Approach to Molecular Catalysis by 3d Transition Metals: Challenges and Opportunities
Vogiatzis, K. D., Polynski, M. V., Kirkland, J. K., Townsend, J., Hashemi, A., Liu, C., & Pidko, E. A. (2019) · Chemical Reviews · doi:10.1021/acs.chemrev.8b00361 · Cited by 423
Highly Efficient Ruthenium‐Catalyzed N‐Formylation of Amines with H2 and CO2
Zhang, L., Han, Z., Zhao, X., Wang, Z., & Ding, K. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201500939 · Cited by 357
Metadata
- Authors
- Dub, P. A., & Ikariya, T.
- Venue
- ACS Catalysis
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-07-18
- Volume
- 2
- Issue
- 8
- Pages
- 1718-1741
- ISSN
- 2155-5435 (ISSN-L)
- OpenAlex
- W2085639342
- Cited by
- 386
- References
- 63
- FWCI
- 16.96
- Type
- journal article
- Language
- en
- Open access
- closed
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.