2016 Fiscal Year Final Research Report
Development of Coupling Reaction of Enol Derivatives as Electrophiles Using Well-Controlled Lewis Acids
| Project/Area Number |
26810059
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Synthetic chemistry
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| Research Institution | Osaka University |
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Principal Investigator |
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Keywords | カップリング反応 / ルイス酸 |
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| Outline of Final Research Achievements |
A cross-coupling reaction is one of the most important method for carbon-carbon bond formation. Generally, organic halides are used as electrophiles due to high reactivity, but they are expensive and potentially toxic. In contrast, oxygen-based electrophiles such as alcohol-, arenol-, enol-derivatives have attracted much attention. These compounds have several advantages over organic halides. However, this type of coupling reaction is very difficult because of the inert carbon-oxygen bond. I have established coupling reactions using enol ethers with ketene silyl acetals catalyzed by gallium bromide. And, the coupling with silyl ketene imines was also achieved. Both coupling reactions proceed via addition-elimination mechanism involving region- and stereoselective carbometalation.
Various types of enol derivatives, ketene silyl acetals, and silyl ketene imines were applicable.
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| Free Research Field |
有機化学
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