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One-pot synthesis of internal conjugated (Z)-enynyltrimethylsilanes possessing aryl, cycloalkenyl, (E)- or (Z)-alk-1-enyl moieties on the sp carbon atom via two types of cross-coupling reaction
https://kitami-it.repo.nii.ac.jp/records/8448
https://kitami-it.repo.nii.ac.jp/records/84484fdac1ae-ad67-4a6a-83d6-0085e8fd6996
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
f16208ss.pdf (230.2 kB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
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| 公開日 | 2016-08-31 | |||||
| タイトル | ||||||
| タイトル | One-pot synthesis of internal conjugated (Z)-enynyltrimethylsilanes possessing aryl, cycloalkenyl, (E)- or (Z)-alk-1-enyl moieties on the sp carbon atom via two types of cross-coupling reaction | |||||
| 言語 | en | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | (Z)-enynyltrimethylsilane | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | (trimethylsilyl)ethynyl bromide | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | (Z)-1,3-bis(trimethylsilyl)alk-3-en-1-yne | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | Suzuki-type reaction | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | sila-Sonogashira reaction | |||||
| 資源タイプ | ||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
| 資源タイプ | journal article | |||||
| アクセス権 | ||||||
| アクセス権 | open access | |||||
| アクセス権URI | http://purl.org/coar/access_right/c_abf2 | |||||
| 著者 |
Hoshi, Masayuki
× Hoshi, Masayuki× Iizawa, Tomohiko× Okimoto, Mitsuhiro× Shirakawa, Kazuya |
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| 著者別名 | ||||||
| 識別子Scheme | WEKO | |||||
| 識別子 | 44871 | |||||
| 識別子Scheme | KAKEN | |||||
| 識別子URI | https://nrid.nii.ac.jp/ja/nrid/1000000113712 | |||||
| 識別子 | 113712 | |||||
| 姓名 | 星, 雅之 | |||||
| 言語 | ja | |||||
| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | Described herein is an operationally simple and mild method for the stereospecific synthesis of internal conjugated (Z)-enynyltrimethylsilanes whose conjugation is extended away from the distal alkynyl carbon atom. This protocol involves two types of cross-coupling reaction, a Suzuki-type reaction and a sila-Sonogashira reaction, and the desired synthesis can be performed in a one-pot manner. Thus, the copper-mediated cross-coupling reaction of dicyclohexyl[(Z)-1-(trimethylsilyl)alk-1-enyl]boranes with (trimethylsilyl)ethynyl bromide is carried out in the presence of aqueous lithium hydroxide at -15 ?C to room temperature, resulting in the stereospecific formation of (Z)-1,3-bis(trimethylsilyl)alk-3-en-1-ynes. Subsequent reaction is allowed to proceed without isolation of the enynes. Thus, palladium/copper-catalyzed cross-coupling reactions with aryl iodides, cycloalk-1-enyl triflates, and (E)- and (Z)-alk-1-enyl iodides can be accomplished in the presence of either 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or tetrabutylammonium fluoride (TBAF) at ambient temperature to provide the corresponding internal conjugated (Z)-enynyltrimethylsilanes possessing one more sp-sp2 carbon bond. | |||||
| 書誌情報 |
Synthesis 巻 22, p. 3591-3600, 発行日 2008 |
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| DOI | ||||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | http://doi.org/10.1055/s-0028-1083201 | |||||
| 権利 | ||||||
| 権利情報 | c Georg Thieme Verlag Stuttgart ? New York | |||||
| 出版者 | ||||||
| 出版者 | Georg Thieme Verlag | |||||
| 著者版フラグ | ||||||
| 値 | author | |||||
| 出版タイプ | ||||||
| 出版タイプ | AM | |||||
| 出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||
