| Project/Area Number |
10450342
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| Research Category |
Grant-in-Aid for Scientific Research (B).
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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 |
SAITO Seiki Okayama University, Faculty of Engineering, Professor, 工学部, 教授 (60033239)
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| Co-Investigator(Kenkyū-buntansha) |
ISHIKAWA Teruhiko Okayama University, Faculty of Engineering, Instructor, 工学部, 助手 (10263617)
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| Project Period (FY) |
1998 – 2000
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| Project Status |
Completed (Fiscal Year 2000)
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| Budget Amount *help |
¥13,500,000 (Direct Cost: ¥13,500,000)
Fiscal Year 2000: ¥2,600,000 (Direct Cost: ¥2,600,000)
Fiscal Year 1999: ¥2,400,000 (Direct Cost: ¥2,400,000)
Fiscal Year 1998: ¥8,500,000 (Direct Cost: ¥8,500,000)
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| Keywords | aromatization of enamine / aromatization of acyclic enone / aniline derivative / PdCl_2 / nitro aldol reaction / Mannich reaction |
|---|
| Research Abstract |
Enamines prepared from cyclohexanones, cyclohexane-1, 3-diones or tetralones led to aryl amines in one pot when treated with stoichiometric amount of palladium salts [PdCl_2 (MeCN)_2] in acetonitrile in the presence of triethylamine at rt or at elevated temperature in some cases for 5 min-2 h. Initial electrophilic attack of palladium chloride on the β-carbon of the enamines led to a σ-palladium species which triggered a series of reactions destined for aromatization to give aryl amines in good yields. The intervention of such a σ-palladium species has been attested by a trapping experiment. On the basis of this reaction mechanism, we have developed another new process capable of transforming acyclic compounds having 6-en-2-one frameworks to aryl amines when their enamines were treated under the similar conditions as above, featuring again the formation of σ-palladium species as the initial key intermediate.
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