| Project/Area Number |
25620085
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Multi-year Fund |
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| Research Field |
Synthetic chemistry
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| Research Institution | Hiroshima University |
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Principal Investigator |
KOMEYAMA Kimihiro 広島大学, 工学(系)研究科(研究院), 助教 (80432681)
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| Project Period (FY) |
2013-04-01 – 2015-03-31
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| Project Status |
Completed (Fiscal Year 2014)
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| Budget Amount *help |
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2014: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2013: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
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| Keywords | 鉄 / ラジカル / カップリング / ビアリール / ヘテロ芳香族化合物 / 芳香族ボロン酸 / アリール化反応 / アリールラシカル / アリールボロン酸 / 直接アリール化反応 |
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| Outline of Final Research Achievements |
We found that iron reagents like FeSO4 was effective reagent for the generation of aryl radicals from arylboronic acids. For its synthetic applications, we achieved a direct arylation of benzoquinones with the generated aryl radicals from the bronco acids, in which a diverse set of monoarylated benzoquinones were obtained in good yields. In addition, addition of ascorbic acids to the reaction media or replacement of benzoquinones by hydroquinones made the iron-mediated arylation change to catalytic reaction. Furthermore, we tried to a direct arylation of heteroarenes by means of iron-mediated aryl radical generation, wherein many type of heteroarenes such as pyridines, pyridine, pyrimidines could participated in the arylation. To gain a insight of the radical generation process, we investigated the process by DFT calculation. As a results, electron density on the aryl ring of moronic acids strongly depended on the efficiency of the radical generation process.
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