Efficient Chemoselective Reduction of N ‐Oxides and Sulfoxides Using a Carbon‐Supported Molybdenum‐Dioxo Catalyst and Alcohol
Abstract
Abstract The chemoselective reduction of a wide range of N ‐oxides and sulfoxides with alcohols is achieved using a carbon‐supported dioxo‐molybdenum ( Mo@C ) catalyst. Of the 10 alcohols screened, benzyl alcohol exhibits the highest reduction efficiency. A variety of N ‐oxide and both aromatic and aliphatic sulfoxide substrates bearing halogens as well as additional reducible functionalities are efficiently and chemoselectively reduced with benzyl alcohol. Chemoselective N ‐oxide reduction is effected even in the presence of potentially competing sulfoxide moieties. In addition, the Mo@C catalyst is air‐ and moisture‐stable, and is easily separated from the reaction mixture and then re‐subjected to reaction conditions over multiple cycles without significant reactivity or selectivity degradation. The high stability and recyclability of the catalyst, paired with its low toxicity and use of earth‐abundant elements makes it an environmentally friendly catalytic system.
- Authors:
-
[2];
- Department of Chemistry Northwestern University 2145 Sheridan Road, Evanston Illinois 60208 USA
- Department of Chemistry Northwestern University 2145 Sheridan Road, Evanston Illinois 60208 USA, Current Address Shell Catalysts &, Technologies Shell Technology Center Houston 3333 Highway 6 South Houston Texas 77082 USA
- Publication Date:
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1512828
- Resource Type:
- Publisher's Accepted Manuscript
- Journal Name:
- ChemCatChem
- Additional Journal Information:
- Journal Name: ChemCatChem Journal Volume: 11 Journal Issue: 16; Journal ID: ISSN 1867-3880
- Publisher:
- Wiley Blackwell (John Wiley & Sons)
- Country of Publication:
- Germany
- Language:
- English
Citation Formats
Li, Jiaqi, Liu, Shengsi, Lohr, Tracy L., and Marks, Tobin J.. Efficient Chemoselective Reduction of N ‐Oxides and Sulfoxides Using a Carbon‐Supported Molybdenum‐Dioxo Catalyst and Alcohol. Germany: N. p., 2019.
Web. doi:10.1002/cctc.201900436.
Li, Jiaqi, Liu, Shengsi, Lohr, Tracy L., & Marks, Tobin J.. Efficient Chemoselective Reduction of N ‐Oxides and Sulfoxides Using a Carbon‐Supported Molybdenum‐Dioxo Catalyst and Alcohol. Germany. https://doi.org/10.1002/cctc.201900436
Li, Jiaqi, Liu, Shengsi, Lohr, Tracy L., and Marks, Tobin J.. Wed .
"Efficient Chemoselective Reduction of N ‐Oxides and Sulfoxides Using a Carbon‐Supported Molybdenum‐Dioxo Catalyst and Alcohol". Germany. https://doi.org/10.1002/cctc.201900436.
@article{osti_1512828,
title = {Efficient Chemoselective Reduction of N ‐Oxides and Sulfoxides Using a Carbon‐Supported Molybdenum‐Dioxo Catalyst and Alcohol},
author = {Li, Jiaqi and Liu, Shengsi and Lohr, Tracy L. and Marks, Tobin J.},
abstractNote = {Abstract The chemoselective reduction of a wide range of N ‐oxides and sulfoxides with alcohols is achieved using a carbon‐supported dioxo‐molybdenum ( Mo@C ) catalyst. Of the 10 alcohols screened, benzyl alcohol exhibits the highest reduction efficiency. A variety of N ‐oxide and both aromatic and aliphatic sulfoxide substrates bearing halogens as well as additional reducible functionalities are efficiently and chemoselectively reduced with benzyl alcohol. Chemoselective N ‐oxide reduction is effected even in the presence of potentially competing sulfoxide moieties. In addition, the Mo@C catalyst is air‐ and moisture‐stable, and is easily separated from the reaction mixture and then re‐subjected to reaction conditions over multiple cycles without significant reactivity or selectivity degradation. The high stability and recyclability of the catalyst, paired with its low toxicity and use of earth‐abundant elements makes it an environmentally friendly catalytic system.},
doi = {10.1002/cctc.201900436},
journal = {ChemCatChem},
number = 16,
volume = 11,
place = {Germany},
year = {2019},
month = {5}
}
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