2006 Fiscal Year Final Research Report Summary
Development of New Reactions with Organometallic Reagents Stable in
| Project/Area Number |
14078215
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| Research Category |
Grant-in-Aid for Scientific Research on Priority Areas
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| Allocation Type | Single-year Grants |
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| Review Section |
Science and Engineering
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| Research Institution | Kyoto University |
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Principal Investigator |
OSHIMA Koichiro Kyoto University, Department of Material Chemistry, Professor, 工学研究科, 教授 (00111922)
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| Project Period (FY) |
2002 – 2005
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| Keywords | Aqueous Media / Nickel / Trialkylborane / Alkvlation |
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| Research Abstract |
The alkylation of aldehydes with organometallic reagents is one of the most important reactions in organic chemistry. Conventional alkylborane reagents do not react with aldehydes. We disclosed that nickel-catalyzed alkylation of aldehydes with trialkylboranes proceeds smoothly in the presence of a catalytic amount of η^2-ally1-1,2,3,4,5-pentamethy1-1,3-cyclopentadiene or an excess of cesium carbonate to afford the corresponding secondary alcohols. Trialkylboranes prepared from borane-dimethyl sulfide and terminal olefins via hydroboration as well as commercially available trialkylboranes could be employed for the reaction. The reaction would proceed via 12-coordinated nickel complexes with aldehydes as key intermediates. Interestingly, water enabled alkylation of aldehydes with trialkylboranes under nickel catalysis without additives.
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