C-F Bond Activation for Synthetic Organofluorine Chemistry ; Survey of Metals and Application for New Reactions
| Project/Area Number |
17550104
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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 |
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Principal Investigator |
UNEYAMA Kenji Okayama University, School of Natural Science, Professor, 大学院自然科学研究科, 教授 (00033150)
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| Co-Investigator(Kenkyū-buntansha) |
KATAGIRI Toshimasa Okayama University, School of Natural Science, Associate Professor, 大学院自然科学研究科, 助教授 (70202009)
TAKAGI Jun Okayama University, School of Natural Science, Research Associate, 大学院自然科学研究科, 助手 (20379712)
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| Project Period (FY) |
2005 – 2006
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| Project Status |
Completed (Fiscal Year 2006)
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| Budget Amount *help |
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2006: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 2005: ¥2,400,000 (Direct Cost: ¥2,400,000)
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| Keywords | Defluorination / Organic fluorine Compound / Difluoro / magnesium / Difluoropyruvates / ジフルオロ化合物 |
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| Research Abstract |
1) Survey metals suitable for defluorination:
In order to develop a synthetic method for difluorinated organic compounds, a series of survey of metals feasible for effective defluorination of trifluoromethyl ketones have been conducted. Among a total of 26 main group, transition, and lanthanide metals examined, magnesium was found to be the best for effective defluorination from the points of strong reducing power, easy handling, economical feasibility, and wastability,.
2) Application of the present defluorination protocol for new reactions
2-1)Reaction of trifluoroacetimidoyl iodides with metal magnesium in the presence of TMSC1 provided a double silylated difluoroenamines in excellent yields.
2-2) Non-defluorinative functionalization of methyl trifluoropyruvate under the same conditions provided the corresponding ketenesilyl acetals, which are umpolungs for the pyruvates.
2-3) Fluoride ion-catalyzed desilylative-defluorination provided difluoroacrylates which can be transformed to 3-substituted3,3-difluoropyruvates.
2-4) Reaction of trifluoroacetyl chloride with magnesium in the presence of TMSC1 provided trifluoroacetyl silane.
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Report
(3 results)
Research Products
(15 results)
