Copper-catalyzed C(sp3)-H functionalization for the synthesis of various heterocyclic compounds
| Project/Area Number |
17K15418
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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 |
Chemical pharmacy
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| Research Institution | Tohoku University |
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Principal Investigator |
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| Project Period (FY) |
2017-04-01 – 2019-03-31
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| Project Status |
Completed (Fiscal Year 2018)
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| Budget Amount *help |
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2018: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
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| Keywords | 炭素－水素結合官能基化 / 複素環化合物 / 銅触媒 / 酸化反応 / イソインドリノン / ラクトン / 触媒・化学プロセス / 炭素ー水素結合官能基化 / β-ラクタム / 有機化学 / C-H官能基化 / 遷移金属 |
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| Outline of Final Research Achievements |
Direct functionalization of C－H bonds is a highly attractive method because it does not require any pre-functionalized starting materials. Therefore, this method can attain the atom- and step-economic synthesis of organic compounds. We have developed copper-catalyzed C(sp3)－H functionalization of 2-alkyl-N-arylbenzamides for the synthesis of N-aryl-isoindolinones. In this study, this method was applied to the synthesis of bioactive compounds, indoprofen and DWP205190. Furthermore, we developed a novel C(sp3)-H bond lactonization of 2-alkylbenzoic acids using peroxydisulfate as the sole oxidant.
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| Academic Significance and Societal Importance of the Research Achievements |
C(sp3)－H結合の官能基化により，含sp3炭素複素環化合物であるイソインドリノンやラクトンの実用的な合成法を確立することができた．本手法は今後様々な複素環骨格構築法に応用していくことができると考えている．また，本研究成果により，直截的に生理活性物質や機能性材料の基本骨格として多く存在する含 sp3 炭素複素環化合物を安価かつ効率的に合成することが可能になると考えられ，医学・薬学・材料科学等の広範な分野に大きく貢献できる．
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Report
(3 results)
Research Products
(26 results)
