Journal
ORGANOMETALLICS
Volume 35, Issue 7, Pages 982-989Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.organomet.6b00009
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Funding
- National Science Foundation [CHE-1362501]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1362501] Funding Source: National Science Foundation
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Ruthenium complexes supported by two new CNN-pincer ligands were synthesized. Both were tested as catalysts for the hydrogenation of esters under mild conditions (105 degrees C, 6 bar H-2). A striking dependence on ligand structure was observed, as a dimethylamino-substituted ligand gave a nearly inactive catalyst, while a diethylamino-substituted variant gave up to 980 catalytic turnovers for the hydrogenation of benzyl benzoate. This system catalyzes the hydrogenation of various substrates including ethyl, benzyl, and hexyl esters, but is surprisingly unreactive toward methyl esters. Experiments demonstrate that base-catalyzed transesterification is rapid under the reaction conditions and that methyl esters are effectively hydrogenated when benzyl alcohol is added to the reaction mixture. The reverse reaction, dehydrogenation of primary alcohols to give esters, was tested as well; up to 920 catalytic turnovers were observed for the dehydrogenation of 1-hexanol to hexyl hexanoate.
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