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.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 4139-4146 |
| Number of pages | 8 |
| Journal | ChemCatChem |
| Volume | 11 |
| Issue number | 16 |
| DOIs | |
| State | Published - Aug 21 2019 |
Funding
This work is supported by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Award Number DOE DE-FG02-03ER15457 to the Institute for Catalysis in Energy Processes (ICEP) at Northwestern University (J.L., S.L.). This work made use of the Integrated Molecular Structure Education and Research Center (IMSERC) at Northwestern U., which has received support from the NSF CHE-1048773, NSF CHE-9871268; Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource (NSF ECCS-1542205); the State of Illinois and International Institute for Nanotechnology (IIN). This work made use of the Keck-II facility of the NUANCE Center at Northwestern U., which has received support from the Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource (NSF ECCS-1542205); the MRSEC program (NSF DMR-1720139) at the Materials Research Center; the International Institute for Nanotechnology (IIN); the Keck Foundation; and the State of Illinois, through the IIN. This work made use of the Quantitative Bio-element Imaging Center (QBIC) at Northwestern University. This work made use of the Jerome B. Cohen X-Ray Diffraction Facility supported by the MRSEC program of the National Science Foundation (DMR-1720139) at the Materials Research Center of Northwestern University and the Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource (NSF ECCS-1542205). We thank our Dr. Yang Wang at Northwestern University who generously provided insight and expertise that assisted the research.
Keywords
- Carbon-supported Dioxo-Molybdenum
- Chemoselective
- Environmentally Friendly
- Heterogeneous Catalysis
- N-oxide and Sulfoxide Reduction
ASJC Scopus subject areas
- Catalysis
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry