Catalytic Activation of Carbon-Fluorine Bonds by Low-valent Niobium Species
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- Akiyama Takahiko
- Department of Chemistry, Faculty of Science, Gakushuin University
Bibliographic Information
- Other Title
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- 低原子価ニオブ種による炭素-フッ素結合の触媒的活性化反応
- テイゲンシカ ニオブシュ ニ ヨル タンソ フッソ ケツゴウ ノ ショクバイテキ カッセイカ ハンノウ
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Abstract
It was found that low-valent niobium species, which is generated from niobium(V) chloride and lithium aluminum hydride, in situ, is an efficient catalyst for activation of carbon-fluorine bonds. The low-valent niobium species catalyzed 1) hydrodefluorination of fluorobenzenes and α,α,α-trifluorotoluenes, and 2) intramolecular C-C coupling reactions of o-aryl-, o-alkenyl-, and o-alkylamino-α,α,α-trifluorotoluenes. In the latter reactions, fluorenes, indenes, and N-fused indoles were synthesized catalytically in good yields. Nb(0) is supposed to be an active species. Deuterium labeling experiments suggest that niobium fluorocarbenoid intermediates are generated from α,α,α-trifluorotoluenes in the latter C-C coupling reactions.
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 67 (3), 208-218, 2009
The Society of Synthetic Organic Chemistry, Japan
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Details
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- CRID
- 1390001205311352448
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- NII Article ID
- 10024967911
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- NII Book ID
- AN0024521X
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- COI
- 1:CAS:528:DC%2BD1MXjsFWjsrk%3D
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- ISSN
- 18836526
- 00379980
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- NDL BIB ID
- 10205840
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed