Journal
CHEMCATCHEM
Volume 11, Issue 16, Pages 4139-4146Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201900436
Keywords
Chemoselective; N-oxide and Sulfoxide Reduction; Carbon-supported Dioxo-Molybdenum; Environmentally Friendly; Heterogeneous Catalysis
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Funding
- U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences [DOE DE-FG02-03ER15457]
- NSF [CHE-9871268, ECCS-1542205]
- Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource (NSF) [ECCS-1542205]
- State of Illinois
- International Institute for Nanotechnology (IIN)
- MRSEC program (NSF) at the Materials Research Center [DMR-1720139]
- Keck Foundation
- State of Illinois, through the IIN
- MRSEC program of the National Science Foundation at the Materials Research Center of Northwestern University [DMR-1720139]
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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.
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