2010 Fiscal Year Final Research Report
Development of New Cascade Type Reactions Catalyzed by Metal Hydrides
| Project/Area Number |
21750106
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | Osaka Prefecture University |
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Principal Investigator |
FUKUYAMA Takahide Osaka Prefecture University, 理学系研究科, 准教授 (60332962)
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| Project Period (FY) |
2009 – 2010
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| Keywords | 遷移金属ヒドリド / 連続結合形成 / 触媒反応 / ヒドロメタル化 |
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| Research Abstract |
This research aimed at development of new catalytic reactions in which metal hydride species play a key role. The reaction of benzylic alcohols with α,β-unsaturated aldehydes in the presence of ruthenium-hydride gave α-hydroxymethyl ketones. α-Hydroxymethyl ketones underwent retro-aldol reaction in fluorous-organic hybrid solvent, F-626. One-pot procedure for the synthesis of ketones has also been achieved by the consecutive ruthenium hydride-catalyzed reaction and the thermal retro-aldol reaction. RuHCl(CO)(PPh_3)_3 effectivly catalyzed intramolecular Tishchenko reaction. The reaction of enones with dialdehydes gave keto lactons in good yields via sequential C-C and CO bond formation. Boronic acids react with aldehydes in the presence of RuHCl(CO)(PPh_3)_3 to give ketones. Ir catalyzed decarbonylation took place to give internal olefins, where addition of KI dramatically accelerated the decarbonylation reactions. Ir-H species formed in situ catalyzed isomerization of olefins.
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