2002 Fiscal Year Final Research Report Summary
Organic Synthesis using Silicone as all Organosilicon Reagent
| Project/Area Number |
13650915
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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 | Tokyo Institute of Technology |
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Principal Investigator |
MORI Atsunori Tokyo Institute of Technology, Chemical Resources Laboratory, Associate Professor, 資源化学研究所, 助教授 (90210111)
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| Project Period (FY) |
2001 – 2002
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| Keywords | silicone / organosilicon reagent / cyclic siloxane / polysiloxane / cross-coupling reaction / conjugate addition / tetrabutylammonium fluoride / Mizoroki-Heck-type reaction |
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| Research Abstract |
This research pursued for the purpose of carrying out synthetic organic reactions using silicone as a new class of organosilicon reagent. Silicone bearing an aryl or alkenyl group on the silicon atom was employed for several carbon-carbon bond-forming reactions. Cyclic or polymeric silicone reagent was use for the reaction. In particular, poly (phenylmethylsiloxane), which is a commercially available highly thermo-resistant silicone oil, affected palladium-catalyzed cross-coupling reaction with organic halides to give biaryl derivatives that are potentially available for liquid crystalline organic materials. Alkenylsiloxanes, which was prepared from commercially available PMHS ; poly (methylhydrosiloxane) with alkyne via hydrosilylation, also affected cross-coupling reactions. In these reactions TBAF (tetrabutylammonium fluoride) or Ag_2O served as an effective activator for the reaction. Rhodium-catalyzed reaction of alfa. Beta-unsaturated carbonyl compounds also took place to give the conjugate addition products. On the other hand, the reaction of organosilicon reagents catalyzed by indium complexes brought about the Mizoroki-Heck-type reaction.
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