Application of the late main group metal active species for the synthesis of nitrogen-containing organic compounds
| Project/Area Number |
17K08232
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Institute of Physical and Chemical Research |
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Principal Investigator |
Takimoto Masanori 国立研究開発法人理化学研究所, 開拓研究本部, 専任研究員 (50312377)
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| Project Period (FY) |
2017-04-01 – 2020-03-31
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| Project Status |
Completed (Fiscal Year 2019)
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| Budget Amount *help |
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2019: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2018: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2017: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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| Keywords | 有機亜鉛 / アレナミド / 含窒素有機化合物 / 銅触媒 / N-ヘテロサイクリックカルベン / 炭素ー炭素結合形成 / 二官能基化 / N－ヘテロサイクリックカルベン / 炭素－炭素結合 / カルボ亜鉛化 / C-Hメタル化 / 希土類触媒 / イナミド / ピリジン類 / 多成分付加反応 / 有機合成化学 / 有機金属化学 / 触媒化学 |
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| Outline of Final Research Achievements |
Nitrogen containing organic compounds are frequently found in biologically active compounds and are also important as synthetic intermediates for functional materials such as pharmaceuticals. In this study, development of novel organozinc species containing a nitrogen functional group and utilization of such species for the synthesis of nitrogen containing organic compounds have been examined. Accordingly, it was found that an NHC-copper salt could catalyze carbozincation of allenamides with dialkylzinc reagents in regioselective manner to form vinylzinc species. Furthermore, the addition of a catalytic amount of paraformaldehyde could greatly accelerated the present carbozincation process. The generated vinylzinc species could be used for various carbon-carbon formation reactions such as palladium-catalyzed cross-coupling reactions.
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| Academic Significance and Societal Importance of the Research Achievements |
分子内に窒素原子を有する有機化合物（含窒素有機化合物）は、生物活性天然物やアミノ酸をはじめとする生体機能分子の多くを構成する重要な化合物群である。また、医薬品や機能性有機材料などとしても重要であり、含窒素有機化合物の効率的合成法の開発は有機合成化学的に重要な研究課題の一つである。本研究では含窒素化合物の一つであるエナミドを、銅触媒による位置選択的カルボ亜鉛化と、生成したビニル亜鉛種と各種求電子試薬との連続的炭素-炭素結合形成反応によって合成可能とした。これは、特に、従来の方法では合成困難な、多置換エナミドの有用な合成法になり得る。
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Report
(4 results)
Research Products
(4 results)
