1996 Fiscal Year Final Research Report Summary
Exploitation of New Synthetic Reactions via C-H Bond Activation by Transition Metal Catalysts
| Project/Area Number |
07455363
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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 | KYUSHU UNIVERSITY |
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Principal Investigator |
FUJIWARA Yuzo Kyushu Univ. Fac. of Eng., Dep't of Chemical Science and Technology, Professor, 工学部, 教授 (10029481)
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| Co-Investigator(Kenkyū-buntansha) |
NAGATA Kensuke Kyushu Univ. Fac. of Eng., Dep't of Chemical Science and Technology, Assistant, 工学部, 助手 (40264080)
TANIGUCHI Yuki Kyushu Univ. Fac. of Eng., Dep't of Chemical Science and Technology, Assistant, 工学部, 助手 (50217139)
KITAMURA Tsugio Kyushu Univ. Fac. of Eng., Dep't of Chemical Science and Technology, Associate P, 工学部, 助教授 (00153122)
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| Project Period (FY) |
1995 – 1996
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| Keywords | C-H Bond Activation / Carbon Monoxide / Alkane / Arene / Aminomethylation / Aromatic Acid / Amine Synthesis / Propane |
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| Research Abstract |
Our research on this project has discovered and developed the following two new synthetic reactions : 1) carboxylation of arenes with CO by palladium catalysts under very mild conditions, and 2) aminomethylation of alkanes with methyl-tert-amine N-oxides by copper catalysts.
1. Carboxylation of Arenes with CO by Palladium Catalysts under Very Mild Conditions
(1) The Pd (OAc)_2 catalyzed carboxylation reaction of aromatic compounds such as benzene, toluene, anisole, chlorobenzene, and naphthalene with CO in the presence of trifluoroacetic acid and K_2S_2O_8, to give the corresponding aromatic carboxylic acids in high yields under the vary mild conditions (1 atm CO,room temperature) has been discovered.
(2) The reaction proceeds electrophilically with o, p-orientation when an electron-releasing group is attached to the benzene ring.
2. Aminomethylation of Alkanes with Methyl-tert-amine N-oxides by Copper Catalysts
(1) The Cu (OAc)_2/K_2S_2O_8/CF_3 COOH system has been found to cause the aminomethylation reaction of alkanes (10 atm) with methyl-tert-amine N-oxidess at 150ﾟC to give the corresponding amines in high yields.
(2) Reactions of propane and ethane with trimetjylamine N-oxide gives N,N'-dimethylisobutylamine and N,N'-dimethylpropylamine, respectively. But methane remains unreacted under the present reaction conditions and the work is underway.
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