2007 Fiscal Year Final Research Report Summary
Synthesis of Tetraethynylsilane
| Project/Area Number |
18550101
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Okayama University of Science |
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Principal Investigator |
ORITA Akihiro Okayama University of Science, Department of Chemistry, Assistant Professor (30262033)
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| Project Period (FY) |
2006 – 2007
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| Keywords | Organic Synthesis / Silane / Aryleneethynylene / Double elimination / Sulfone / Aldehyde |
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| Research Abstract |
For preparation of arylethynes, Sonogashira coupling of aryl halide with terminal acetylene has been utilized routinely in the presence of transition metal catalysts. In contrast to this, we have developed a new methodology for synthesis of arylethynes in which no transition metal-catalyst is required. When a THF solution of benzyl phenyl sulfone is treated with base, arylaldehyde and chloro diethylphosphate, the desired diarylethyne is obtained successfully. This protocol is versatile because base-sensitive functional groups such as halogen and/or TMS-ethynyl group are not damaged. These functionalized acetylenes can be utilized as building blocks for construction of aryleneethynylenes having highly extended π systems. For instance, after desilylation of TMS-ethynyl group, tetraethynylsilane can be prepared by reaction of silicone tetrachloride with acetylide which was prepared by treatment of terminal acetylene with Grignard reagent. The tetraethynylsilane exhibited high quantum yield according to the number of arylene-ethynylene moieties.
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