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  1. 学術雑誌掲載済論文
  2. 洋雑誌

Preparation of (E)-1-alkenylboronic acid pinacol esters via transfer of alkenyl group from boron to boron.

https://kitami-it.repo.nii.ac.jp/records/7174
d1bfaa20-e37b-4acf-9d1b-811409f0b7db
名前 / ファイル ライセンス アクション
4610.pdf 4610.pdf (147.9 kB)
Item type 学術雑誌論文 / Journal Article(1)
公開日 2007-05-11
タイトル
言語 en
タイトル Preparation of (E)-1-alkenylboronic acid pinacol esters via transfer of alkenyl group from boron to boron.
言語
言語 eng
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 Shirakawa, Kazuya

× Shirakawa, Kazuya

WEKO 36499

en Shirakawa, Kazuya

Search repository
Arase, Akira

× Arase, Akira

WEKO 36500

en Arase, Akira

Search repository
Hoshi, Masayuki

× Hoshi, Masayuki

WEKO 36501

en Hoshi, Masayuki

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 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
DOI
関連識別子
識別子タイプ DOI
関連識別子 http://doi.org/10.1055/s-2004-829165
権利
権利情報 http://www.thieme-connect.de/ejournals/abstract/synthesis/doi/10.1055/s-2004-829165
権利
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
内容記述タイプ Other
内容記述 application/pdf
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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