| Item type |
学術雑誌論文 / Journal Article(1) |
| 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 |
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
Iizawa, Tomohiko
Okimoto, Mitsuhiro
Shirakawa, Kazuya
|
| 著者別名 |
|
|
|
識別子Scheme |
WEKO |
|
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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 |
|
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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 |
|
|
|
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 |
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|
出版者 |
Georg Thieme Verlag |
| 著者版フラグ |
|
|
言語 |
en |
|
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 |
f16208ss.pdf (230.2 kB)
