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Tandem Frustrated Lewis Pair/Tris(pentafluorophenyl)borane-Catalyzed Deoxygenative Hydrosilylation of Carbon Dioxide
Abstract
The frustrated Lewis pair system consisting of 2 equiv of 2,2,6,6-tetramethylpiperidine (TMP) and tris(pentafluorophenyl)borane [B(C(6)F(5))(3)] activates carbon dioxide to form a boratocarbamate-TMPH ion pair. In the presence of triethylsilane, this species is converted to a silyl carbamate and the known ion pair [TMPH](+)[HB(C(6)F(5))(3)](-), which recently was shown to react with CO(2) via transfer of the hydride from the hydridoborate to form the formatoborate [TMPH](+)[HC(O)OB(C(6)F(5))(3)](-). In the presence of extra B(C(6)F(5))(3) (0.1-1.0 equiv) and excess triethylsilane, the formatoborate is rapidly hydrosilated to form a formatosilane and regenerate [TMPH](+)[HB(C(6)F(5))(3)](-). The formatosilane in turn is rapidly hydrosilated by the B(C(6)F(5))(3)/Et(3)SiH system to CH(4), with (Et(3)Si)(2)O as the byproduct. At low [Et(3)SiH], intermediate CO(2) reduction products are observed; addition of more CO(2)/Et(3)SiH results in resumed hydrosilylation, indicating that this is a robust, living tandem catalytic system for the deoxygenative reduction of CO(2) to CH(4).
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Citations
Cited by
Wang, Q., Zhao, W., He, J., Zhang, Y., & Chen, E. Y.-X. (2017) · Macromolecules · doi:10.1021/acs.macromol.6b02398 · Cited by 127
Heterogeneous reduction of carbon dioxide by hydride-terminated silicon nanocrystals
Sun, W., Qian, C., He, L., Ghuman, K. K., Wong, A. P. Y., Jia, J., Ali, F. M., O’Brien, P. G., Reyes, L. M., Wood, T. E., et al. (2016) · Nature Communications · doi:10.1038/ncomms12553 · Cited by 113
Metadata
- Authors
- Berkefeld, A., Piers, W. E., & Parvez, M.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-07-15
- Volume
- 132
- Issue
- 31
- Pages
- 10660-10661
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2017267600
- Cited by
- 512
- References
- 0
- FWCI
- 23.21
- Type
- journal article
- Language
- en
- Open access
- closed
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- Berkefeld, A., Piers, W. E., & Parvez, M. (2010). Tandem Frustrated Lewis Pair/Tris(pentafluorophenyl)borane-Catalyzed Deoxygenative Hydrosilylation of Carbon Dioxide. Journal of the American Chemical Society. https://doi.org/10.1021/ja105320c
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