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US 5,220,020 AGranted
Catalytic reduction of organic carbonyls using metal catalysts
AssigneeMassachusetts Institute of Technology
InventorsStephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
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Abstract
A process is provided whereby organic carbonyl substrates, including esters, lactones, ketones, amides and imides are reduced in a reaction with a silane reducing reagent and a catalyst. Exemplary catalysts include metal alkoxides and metal aryloxides.
Claims16
A process for catalytically reducing organic carbonyl compounds, comprising the steps of:
- providing a stoichiometric quantity of a silane reducing agent able to contribute a hydride ion during the reduction reaction, a catalytic amount of a catalyst selected from the group consisting of M(L) (L') (L''), M(L) (L') (L'') (L'''), M(L) (L') (L'') (L''') (L.sup.iv), and M(L) (L') (L'') (L''') (L.sup.iv) (L.sup.v), where M is a group 3, 4, 5 or 6 metal, a lanthanide or an actinide and L, L', L'', L''', L.sup.iv, L.sup.v, independently, are some combination of H, an alkyl, an aryl, a silyl, a halogen, --OR, --SR, or --NR(R'), where R and R' are H, an alkyl or aryl and are different or the same, and a stoichiometric quantity of an organic carbonyl substrate selected from the group consisting of esters, lactones, amides and imides;
- reacting the organic carbonyl substrate in the presence of the catalyst and the silane compound at a temperature between 25.degree. and 80.degree. C.;
- and
- recovering and purifying the reaction product.
1 more element
A process for catalytically reducing organic carbonyl compounds, comprising the steps of:
- providing a stoichiometric quantity of a silane reducing agent able to contribute a hydride ion during the reduction reaction, a catalytic amount of an air stable catalyst selected from the group consisting of M(L) (L') (L''), M(L) (L') (L'') (L'''), M(L) (L') (L'') (L''') (L.sup.iv), and M(L) (L') (L'') (L''') (L.sup.iv) (L.sup.v), where M is a group 3, 4, 5 or 6 metal, a lanthanide or an actinide and L, L', L'', L''', L.sup.iv, L.sup.v, independently, are some combination of H, an alkyl, an aryl, a silyl, a halogen, --OR, --SR, or --NR(R'), where R and R' are H, an alkyl or aryl and are different or the same, and a stoichiometric quantity of an organic carbonyl substrate selected from the group consisting of esters, lactones, amides and imides;
- reacting the organic carbonyl substrate in the presence of the catalyst and the silane compound at a temperature between 25.degree. and 80.degree. C.;
- and
- recovering and purifying the reaction product.
1 more element
Dependencies are inferred from the claim text.