| 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 |
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 |
en |
| 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
Okimoto, Mitsuhiro
Nakamura, Shingo
Takahashi, Shinya
|
| 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 |
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 |
|
|
|
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 |
|
|
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 |
f75711ss.pdf (164.0 kB)
