Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 5, Issue 12, Pages 11752-11760Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.7b03298
Keywords
Mechanochemistry; Carbonyl reduction; PMHS; HMF; Polyketone; Transfer hydrogenation
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Funding
- Natural Science and Engineering Research Council of Canada (NSERC)
- Canada Foundation for Innovation (CFI)
- Canada Research Chairs (CRC)
- Fonds de Recherche sur la Nature et les Technologies (FQRNT)
- Center for Green Chemistry and Catalysis (CGCC)
- McGill University
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We report herein a new methodology for the rapid and selective reduction of carbonyls in the solid phase. By exploiting mechanical energy and using a cheap and air-stable silane, polymethylhydrosiloxane (PMHS), we can reduce a variety of carbonyl compounds, with catalytic amounts of fluorides. A scope of 19 substrates was explored to probe the generality of the method. In addition, an important biomass based platform chemical, 5-hydroxymethylfurfural (5-HMF), and an insoluble polymer, polyketone, could be reduced with this methodology. A mechanistic study is also presented, suggesting the active role of volatile silane species. This method is particularly appealing to overcome substrate solubility issues and reduce solvent reliance in organic synthesis.
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