Synthesis of Diketones and ω-Hydroxy Ketones from Methyl Ketones and α,ω-Diols by an [IrCl(cod)]2/PPh3/KOH System
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- Maeda Kensaku
- Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University High Technology Research Center, Kansai University
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- Obora Yasushi
- Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University High Technology Research Center, Kansai University
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- Sakaguchi Satoshi
- Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University High Technology Research Center, Kansai University
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- Ishii Yasutaka
- Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University High Technology Research Center, Kansai University
書誌事項
- タイトル別名
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- Synthesis of Diketones and .OMEGA.-Hydroxy Ketones from Methyl Ketones and .ALPHA.,.OMEGA.-Diols by an [IrCl(cod)]2/PPh3/KOH System
抄録
ω-Hydroxy ketones and diketones, which are important starting materials for the synthesis of cycloalkanones and heterocyclic compounds, were prepared by the one-step reaction of methyl ketones with α,ω-diols under the influence of an iridium complex and a base. The selectivity of ω-hydroxy ketones and diketones could be controlled by varying the starting ratio of methyl ketones to α,ω-diols. For example, reaction using acetophenone (5 equiv) with respect to 1,6-hexanediol (1 equiv) in the presence of [IrCl(cod)]2, PPh3, and KOH without solvent gave 1,10-diphenyl-1,10-decanedione in almost quantitative yield, while reaction using acetophenone (1 equiv) to 1,6-hexanediol (4 equiv) led to 8-hydroxy-1-phenyl-1-octanone in 92% yield. This methodology was successfully extended to the reaction of arylacetonitriles with α,ω-diols leading to diaryldinitriles.
収録刊行物
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 81 (6), 689-696, 2008
公益社団法人 日本化学会
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詳細情報 詳細情報について
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- CRID
- 1390282679119022592
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- NII論文ID
- 130004152474
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- ISSN
- 13480634
- 00092673
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- Crossref
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可