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  1. 学術雑誌掲載済論文
  2. 和雑誌

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
4fdac1ae-ad67-4a6a-83d6-0085e8fd6996
名前 / ファイル ライセンス アクション
f16208ss.pdf f16208ss.pdf (230.2 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 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
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 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 44488

en Hoshi, Masayuki

Search repository
Iizawa, Tomohiko

× Iizawa, Tomohiko

WEKO 44489

en Iizawa, Tomohiko

Search repository
Okimoto, Mitsuhiro

× Okimoto, Mitsuhiro

WEKO 44490

en Okimoto, Mitsuhiro

Search repository
Shirakawa, Kazuya

× Shirakawa, Kazuya

WEKO 44491

en Shirakawa, Kazuya

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 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
DOI
関連識別子
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
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