2013 Fiscal Year Final Research Report
Regioselective Synthesis of Polysubstituted Bneznes by Cross Reaction of Silylated 1,3-Enynes Using Diisobutylaluminum Hydride: Synthesis and Application
| Project/Area Number |
24750082
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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 | Saitama University |
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Principal Investigator |
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| Project Period (FY) |
2012-04-01 – 2014-03-31
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| Keywords | 水素化ジイソブチルアルミニウム / 多置換ベンゼン / 位置選択的合成 / 固体発光 |
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| Research Abstract |
Diisobutylaluminum hydride (DIBAL-H)-promoted reaction of silylated 1,3-enynes provided tetrasubstituted benzenes with complete regioselectivity. The reaction proceeds through dimerization of silylated 1,3-enynes via skeletal rearrengment. Stepwise cross-reaction between two different silylated 1,3-enynes also proceeds to give o,o-bissilylated styrenes in moderate yields. In the latter case, addition of ether enables the stepwise reaction. Silylated acetylenes could also be used instead of the 1,3-enynes. The stilbenes, which could be synthesized by the present reaction, exhibit efficient fluorescence emission in solid and crystal state. The fluorescence quantum yield of one o,o-bissilylstilbenes is 111 times larger than that of dichloromethane solution. Due to the bulky trimethylsilyl group inhibits the crystals from packing tightly to cause concentration quenching. Consequently, the crystals exhibit efficient fluorescence emission.
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