The DOI matches its Crossref record; 7 of the 7 references it cites were found in a registry or an index.
Cyclopentadienone Iron Alcohol Complexes: Synthesis, Reactivity, and Implications for the Mechanism of Iron-Catalyzed Hydrogenation of Aldehydes
Open accessAbstract
Cyclopentadienone iron alcohol complexes generated from the reactions of [2,5-(SiMe(3))(2)-3,4-(CH(2))(4)(eta(5)-C(4)COH)]Fe(CO)(2)H (3) and aldehydes were characterized by (1)H NMR, (13)C NMR, and IR spectroscopy. The benzyl alcohol complex [2,5-(SiMe(3))(2)-3,4-(CH(2))(4)(eta(4)-C(4)CO)]Fe(CO)(2)(HOCH(2)C(6)H(5)) (6-H) was also characterized by X-ray crystallography. These alcohol complexes are thermally unstable and prone to dissociate the coordinated alcohols. The alcohol ligand is easily replaced by other ligands such as PhCN, pyridine, and PPh(3). Dissociation of the alcohol ligand in the presence of H(2) leads to the formation of iron hydride 3. The reduction of aldehydes by 3 was carried out in the presence of both potential intermolecular and intramolecular traps. The reaction of 3 with PhCHO in the presence of 4-methylbenzyl alcohol as a potential intermolecular trapping agent initially produced only iron complex 6-H of the newly formed benzyl alcohol. However, the reaction of 3 with 4-(HOCD(2))C(6)H(4)CHO, which possesses a potential intramolecular alcohol trapping agent, afforded two alcohol complexes, one with the newly formed alcohol coordinated to iron and the other with the trapping alcohol coordinated. The intramolecular trapping experiments support a mechanism involving concerted transfer of a proton from OH and hydride from Fe of 3 to aldehydes. The kinetics and mechanism of the hydrogenation of benzaldehyde catalyzed by 3 are presented.
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Cites
Clapham, S. E., Hadzovic, A., & Morris, R. H. (2004) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2004.04.007 · Cited by 1,316
Ligand-Modulated Palladium-Catalyzed Aerobic Alcohol Oxidations
Sigman, M. S., & Jensen, D. R. (2006) · Accounts of Chemical Research · doi:10.1021/ar040243m · Cited by 578
An Efficient and Chemoselective Iron Catalyst for the Hydrogenation of Ketones
Casey, C. P., & Guan, H. (2007) · Journal of the American Chemical Society · doi:10.1021/ja071159f · Cited by 539
Self-citationNoyori, R., Kitamura, M., & Ohkuma, T. (2004) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0307928100 · Cited by 277
Kimblin, C., Bridgewater, B. M., Churchill, D. G., Hascall, T., & Parkin, G. (2000) · Inorganic Chemistry · doi:10.1021/ic000093l · Cited by 74
Voges, M. H., & Bullock, R. M. (2002) · Journal of the Chemical Society Dalton Transactions · doi:10.1039/b107754f · Cited by 74
Zepik (2001) · doi:10.1002/1521-3773(20010105)40:1
Cited by
Frontiers, Opportunities, and Challenges in Biochemical and Chemical Catalysis of CO 2 Fixation
Appel, A. M., Bercaw, J. E., Bocarsly, A. B., Dobbek, H., DuBois, D. L., Dupuis, M., Ferry, J. G., Fujita, E., Hille, R., Kenis, P. J. A., et al. (2013) · Chemical Reviews · doi:10.1021/cr300463y · Cited by 2,193
Khusnutdinova, J. R., & Milstein, D. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201503873 · Cited by 1,239
Metadata
- Authors
- Casey, C. P., & Guan, H.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-02-04
- Volume
- 131
- Issue
- 7
- Pages
- 2499-2507
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2012092497
- Cited by
- 276
- References
- 7
- FWCI
- 11.17
- Type
- journal article
- Language
- en
- Open access
- green
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