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A Highly Active Phosphine–Borane Organocatalyst for the Reduction of CO2 to Methanol Using Hydroboranes
Open accessAbstract
In this work, we report that organocatalyst 1-Bcat-2-PPh2-C6H4 ((1); cat = catechol) acts as an ambiphilic metal-free system for the reduction of carbon dioxide in presence of hydroboranes (HBR2 = HBcat (catecholborane), HBpin (pinacolborane), 9-BBN (9-borabicyclo[3.3.1]nonane), BH3·SMe2 and BH3·THF) to generate CH3OBR2 or (CH3OBO)3, products that can be readily hydrolyzed to methanol. The yields can be as high as 99% with exclusive formation of CH3OBR2 or (CH3OBO)3 with TON (turnover numbers) and TOF (turnover frequencies) reaching >2950 and 853 h(-1), respectively. Furthermore, the catalyst exhibits "living" behavior: once the first loading is consumed, it resumes its activity on adding another loading of reagents.
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Cited by
Recycling of carbon dioxide to methanol and derived products – closing the loop
Goeppert, A., Czaun, M., Jones, J.-P., Surya Prakash, G. K., & Olah, G. A. (2014) · Chem. Soc. Rev. · doi:10.1039/c4cs00122b · Cited by 1,528
Klankermayer, J., Wesselbaum, S., Beydoun, K., & Leitner, W. (2016) · Angewandte Chemie International Edition · doi:10.1002/anie.201507458 · Cited by 856
Sustainable conversion of carbon dioxide: the advent of organocatalysis
Fiorani, G., Guo, W., & Kleij, A. W. (2015) · Green Chemistry · doi:10.1039/c4gc01959h · Cited by 658
Ganesh, I. (2014) · Renewable and Sustainable Energy Reviews · doi:10.1016/j.rser.2013.11.045 · Cited by 548
Tandem Amine and Ruthenium-Catalyzed Hydrogenation of CO2to Methanol
Rezayee, N. M., Huff, C. A., & Sanford, M. S. (2015) · Journal of the American Chemical Society · doi:10.1021/ja511329m · Cited by 461
Shown, I., Hsu, H.-C., Chang, Y.-C., Lin, C.-H., Roy, P. K., Ganguly, A., Wang, C.-H., Chang, J.-K., Wu, C.-I., Chen, L.-C., et al. (2014) · Nano Letters · doi:10.1021/nl503609v · Cited by 366
Catalytic reduction of CO2into fuels and fine chemicals
Modak, A., Bhanja, P., Dutta, S., Chowdhury, B., & Bhaumik, A. (2020) · Green Chemistry · doi:10.1039/d0gc01092h · Cited by 267
Metadata
- Authors
- Courtemanche, M.-A., Légaré, M.-A., Maron, L., & Fontaine, F.-G.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-06-14
- Volume
- 135
- Issue
- 25
- Pages
- 9326-9329
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2324586646
- Cited by
- 338
- References
- 0
- FWCI
- 18.74
- Type
- journal article
- Language
- en
- Open access
- hybrid
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