Iridium-Catalyzed Transfer Hydrogenation of α,β-Unsaturated and Saturated Carbonyl Compounds with 2-Propanol
- 1 June 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (13) , 4710-4712
- https://doi.org/10.1021/jo0156722
Abstract
The selective transfer hydrogenation of α,β-unsaturated carbonyl compounds to saturated ones was achieved by the use of 2-propanol as a hydrogen donor under the influence of catalytic amounts of [Ir(cod)Cl]2, 1,3-bis(diphenylphosphino)propane (dppp), and Cs2CO3. Thus, a variety of conjugated enones were allowed to react with 2-propanol in the presence of the [Ir(cod)Cl]2/dppp/Cs2CO3 system to give the corresponding saturated carbonyl compounds in good to excellent yields without formation of allylic alcohols. Both dppp and Cs2CO3 were essential components to achieve the reduction satisfactorily. Additionally, the reduction of carbonyl compounds to alcohols was also promoted by the same catalytic system. When the reaction of a 1:1 mixture of a conjugated ketone and a saturated ketone with 2-propanol was carried out in the presence of [Ir(cod)Cl]2 combined with dppp and Cs2CO3, the reduction of the α,β-unsaturated ketone was found to take place in preference to that of the saturated ketone.Keywords
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