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  1. 学術雑誌掲載済論文
  2. 洋雑誌

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
57f395bf-de89-4ae9-80f5-1cb83cb741b1
名前 / ファイル ライセンス アクション
f75711ss.pdf f75711ss.pdf (164.0 kB)
Item type 学術雑誌論文 / Journal Article(1)
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

WEKO 44493

en Hoshi, Masayuki

Search repository
Okimoto, Mitsuhiro

× Okimoto, Mitsuhiro

WEKO 44494

en Okimoto, Mitsuhiro

Search repository
Nakamura, Shingo

× Nakamura, Shingo

WEKO 44495

en Nakamura, Shingo

Search repository
Takahashi, Shinya

× Takahashi, Shinya

WEKO 44496

en Takahashi, Shinya

Search repository
著者別名
姓名
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
DOI
関連識別子
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
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