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Nickel-Mediated Hydrogenolysis of C–O Bonds of Aryl Ethers: What Is the Source of the Hydrogen?
Open accessAbstract
Mechanistic studies of the hydrogenolysis of aryl ethers by nickel were undertaken with (diphosphine)aryl methyl ethers. A Ni(0) complex containing Ni-arene interactions adjacent to the aryl-O bond was isolated. Heating led to aryl-O bond activation and generation of a nickel aryl methoxide complex. Formal β-H elimination from this species produced a nickel aryl hydride which can undergo reductive elimination in the presence of formaldehyde to generate a carbon monoxide adduct of Ni(0). The reported complexes map out a plausible mechanism of aryl ether hydrogenolysis catalyzed by nickel. Investigations of a previously reported catalytic system using isotopically labeled substrates are consistent with the mechanism proposed in the stoichiometric system, involving β-H elimination from a nickel alkoxide rather than cleavage of the Ni-O bond by H(2).
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Cites
The Catalytic Valorization of Lignin for the Production of Renewable Chemicals
Zakzeski, J., Bruijnincx, P. C. A., Jongerius, A. L., & Weckhuysen, B. M. (2010) · Chemical Reviews · doi:10.1021/cr900354u · Cited by 4,468
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Catalytic Transformation of Lignin for the Production of Chemicals and Fuels
Li, C., Zhao, X., Wang, A., Huber, G. W., & Zhang, T. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00155 · Cited by 2,951
Sturgeon, M. R., Kim, S., Lawrence, K., Paton, R. S., Chmely, S. C., Nimlos, M., Foust, T. D., & Beckham, G. T. (2014) · ACS Sustainable Chemistry & Engineering · doi:10.1021/sc400384w · Cited by 414
Homogeneous catalysis for the conversion of biomass and biomass-derived platform chemicals
Deuss, P. J., Barta, K., & de Vries, J. G. (2014) · Catal. Sci. Technol. · doi:10.1039/c3cy01058a · Cited by 316
Deng, W., Zhang, H., Wu, X., Li, R., Zhang, Q., & Wang, Y. (2015) · Green Chemistry · doi:10.1039/c5gc01473e · Cited by 272
Depolymerization of organosolv lignin using doped porous metal oxides in supercritical methanol
Warner, G., Hansen, T. S., Riisager, A., Beach, E. S., Barta, K., & Anastas, P. T. (2014) · Bioresource Technology · doi:10.1016/j.biortech.2014.02.092 · Cited by 108
Metadata
- Authors
- Kelley, P., Lin, S., Edouard, G., Day, M. W., & Agapie, T.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-03-13
- Volume
- 134
- Issue
- 12
- Pages
- 5480-5483
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2074166183
- Cited by
- 160
- References
- 1
- FWCI
- 11.37
- Type
- journal article
- Language
- en
- Open access
- green
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- Kelley, P., Lin, S., Edouard, G., Day, M. W., & Agapie, T. (2012). Nickel-Mediated Hydrogenolysis of C–O Bonds of Aryl Ethers: What Is the Source of the Hydrogen? Journal of the American Chemical Society. https://doi.org/10.1021/ja300326t
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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