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Homo- and heterocoupling of terminal conjugated enynes: One-pot synthesis of alka-1,7-diene-3,5-diynes and alk-1-ene-3,5-diynes via two types of coupling reaction.
https://kitami-it.repo.nii.ac.jp/records/8449
https://kitami-it.repo.nii.ac.jp/records/844957f395bf-de89-4ae9-80f5-1cb83cb741b1
名前 / ファイル | ライセンス | アクション |
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f75711ss.pdf (164.0 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 | ||||||
言語 | en | |||||
タイトル | Homo- and heterocoupling of terminal conjugated enynes: One-pot synthesis of alka-1,7-diene-3,5-diynes and alk-1-ene-3,5-diynes via two types of coupling reaction. | |||||
言語 | ||||||
言語 | eng | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | alkenylborane | |||||
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 | alk-1-en-3-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 | acetylenic coupling | |||||
資源タイプ | ||||||
資源 | http://purl.org/coar/resource_type/c_6501 | |||||
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× Okimoto, Mitsuhiro× Nakamura, Shingo× Takahashi, Shinya |
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著者別名 | ||||||
姓名 | 星, 雅之 | |||||
言語 | ja | |||||
抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | Conjugated dienediynes and enediynes with definite geometry- have been prepared in a one-pot manner. This protocol involves two types of coupling reaction, a Suzuki-type coupling and either a Hay coupling or a Cadiot-Chodkiewicz coupling. Thus, the copper-mediated cross-coupling reaction of (E)-alk-1-enyldisiamylborane with (trimethylsilyl)ethynyl bromide is carried out in the presence of 1 M NaOMe to generate (E)-alk-3-en-1-yne, which is subjected to either palladium/copper-catalyzed homocoupling in the presence of DABCO or copper-catalyzed heterocoupling with 1-iodoalk-1-yne in the presence of TBD or pyrrolidine in a single reaction pot without isolating (E)-alk-3-en-1-yne. The homocoupling has realized the stereoselective construction of (1E,7E)-alka-1,7-diene-3,5-diynes, and the heterocoupling has achieved the formation of (E)-alk-1-ene-3,5-diynes. In addition, starting from (Z)-alk-1-enyldisiamylborane instead of the E-isomer, this series of reactions has led to the formation of (1Z,7Z)-alka-1,7-diene-3,5-diynes and (Z)-alk-1-ene-3,5-diynes, albeit limiting the scope of the substrate. | |||||
書誌情報 |
Synthesis 巻 23, p. 3839-3847, 発行日 2011 |
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DOI | ||||||
識別子タイプ | DOI | |||||
関連識別子 | http://doi.org/10.1055/s-0030-1260253 | |||||
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 |