2006年8月
金属ストロンチウムを用いるBarbier型アルキル化反応の開発
有機合成化学協会誌
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- 巻
- 64
- 号
- 8
- 開始ページ
- 845
- 終了ページ
- 852
- 記述言語
- 日本語
- 掲載種別
- 書評論文,書評,文献紹介等
- DOI
- 10.5059/yukigoseikyokaishi.64.845
Organometallic compounds comprise some of the most versatile reagents in organic synthesis, and among them are organometallic compounds of alkaline-earth elements. Numerous reports have been published on the Grignard (or Barbier) reaction using metallic magnesium and alkyl halides. Furthermore, there are various reports on the preparation and reactivity of the organometallic compounds of calcium and barium. In contrast, fewer studies on the preparation and reactivity of organostrontium compounds were found in the literature. As the results on our investigation, it's found that in the presence of metallic strontium, the Barbier-type alkylation of aldehydes with alkyl iodides proceeded smoothly at-15°C under an argon atmosphere to afford the corresponding alkylated alcohols in moderate to good yields. The Barbier-type alkylation of imines with alkyl iodides also took place smoothly at room temperature under an argon atmosphere to give the corresponding alkylated amines in good yields. Aromatic aldimines reacted with metallic strontium in the presence of a catalytic amount of iodine to obtain the self-coupling products in good yields. Furthermore, the Barbier-type alkylation of esters with alkyl iodides proceeded smoothly at room temperature under an argon atmosphere to afford the corresponding dialkylated alcohols in good yields.
- リンク情報
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- DOI
- https://doi.org/10.5059/yukigoseikyokaishi.64.845
- CiNii Articles
- http://ci.nii.ac.jp/naid/10017652355
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000239772900006&DestApp=WOS_CPL
- URL
- http://ci.nii.ac.jp/naid/10017652355/
- ID情報
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- DOI : 10.5059/yukigoseikyokaishi.64.845
- ISSN : 0037-9980
- CiNii Articles ID : 10017652355
- Web of Science ID : WOS:000239772900006