| Item type |
学術雑誌論文 / Journal Article(1) |
| 公開日 |
2007-05-11 |
| タイトル |
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タイトル |
Preparation of (E)-1-alkenylboronic acid pinacol esters via transfer of alkenyl group from boron to boron. |
|
言語 |
en |
| 言語 |
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|
言語 |
eng |
| 資源タイプ |
|
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資源 |
http://purl.org/coar/resource_type/c_6501 |
|
タイプ |
journal article |
| アクセス権 |
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アクセス権 |
open access |
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アクセス権URI |
http://purl.org/coar/access_right/c_abf2 |
| 著者 |
Shirakawa, Kazuya
Arase, Akira
Hoshi, Masayuki
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| 著者別名 |
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識別子Scheme |
WEKO |
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識別子 |
44871 |
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識別子Scheme |
KAKEN |
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識別子URI |
https://nrid.nii.ac.jp/ja/nrid/1000000113712 |
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識別子 |
113712 |
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姓名 |
星, 雅之 |
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言語 |
ja |
| 抄録 |
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内容記述タイプ |
Abstract |
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内容記述 |
Two synthetic routes to (E)-1-alkenylboronic acid pinacol esters (3) were investigated. Hydroboration of 1-alkynes (1) with 1,3,2-benzodioxaborole (catecholborane), in situ generated by the reaction of BH3 in THF with catechol, proceeded in the presence of a catalytic amount of dicyclohexylborane in THF at room temperature to give the corresponding (E)-1- alkenylboronic acid catechol esters (2). Treatment of the resultant 2 with 2,3-dimethyl-2,3-butanediol (pinacol) easily afforded the desired products 3, which are insensitive to air, moisture and chromatography, in good to high overall yields. The sequential reaction is a highly efficient route to 3 from BH_3 in THF in a one-pot manner. Alternatively, hydroboration of 1 with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacolborane) was achieved in the presence of a catalytic amount of dicyclohexylborane at room temperature under neat conditions to afford the corresponding 3 directly in good to excellent yields. This route is extremely efficient and environmentally benign from the viewpoints of making good use of pinacolborane and of using no solvent, and is capable of using a variety of 1 including functionalized ones such as HC≡CCH_2Cl and HC≡CCH_2OTHP. |
| 書誌情報 |
Synthesis
巻 2004,
号 11,
p. 1814-1820,
発行日 2004-08
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| DOI |
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識別子タイプ |
DOI |
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関連識別子 |
http://doi.org/10.1055/s-2004-829165 |
| 権利 |
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権利情報 |
http://www.thieme-connect.de/ejournals/abstract/synthesis/doi/10.1055/s-2004-829165 |
| 権利 |
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権利情報 |
Georg Thieme Verlag, K. Shirakawa, A. Arase and M. Hoshi, Synthesis, 2004(11), 2004, 1814-1820. c 2004 Georg Thieme Verlag KG. |
| フォーマット |
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内容記述タイプ |
Other |
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内容記述 |
application/pdf |
| 出版者 |
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出版者 |
Georg Thieme Verlag |
|
言語 |
en |
| 著者版フラグ |
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|
言語 |
en |
|
値 |
author |
| 出版タイプ |
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出版タイプ |
AM |
|
出版タイプResource |
http://purl.org/coar/version/c_ab4af688f83e57aa |
4610.pdf (147.9 kB)
