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Title: 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:
 [1];  [1]; ORCiD logo [2];  [1]
  1. Department of Chemistry Northwestern University 2145 Sheridan Road, Evanston Illinois 60208 USA
  2. 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 = {Wed May 15 00:00:00 EDT 2019},
month = {Wed May 15 00:00:00 EDT 2019}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1002/cctc.201900436

Citation Metrics:
Cited by: 12 works
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