アリルアジドの鉄 (((II) ブロミド触媒による分子内C−H結合アミネーション [1,2]-シフトタンデム反応
Quyen Nguyen1, Tuyen Nguyen, Tom G Driver
1Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607-7061, USA.
Journal of the American Chemical Society
|December 26, 2012
まとめ
鉄(II) ブロミドは,C-Hアミネーションと[1,2]-シフトによるアリルアジドからのインドル合成を触媒化する. 反応は,シフトステップでアルキルまたは二次グループよりもフェニルを好む.
科学分野:
- 有機化学 オーガニック・ケミストリー
- カタリシス カタリシス カタリシス
- ヘテロサイクル化学 ヘテロサイクル化学
背景:
- アリルアジドは,有機合成における汎用的な前駆体である.
- インドール・スキャフォールは,医薬品や天然製品に多く見られます.
- C-H機能化は,効率的な合成経路を提供します.
研究 の 目的:
- 2,3-非置換インドルを合成するための新しい触媒方法の開発.
- タンデムC-Hアミネーション/[1,2]-シフト反応のメカニズムを調査する.
- 変換の基質範囲と地域選択性を決定する.
主な方法:
- 鉄(II) ブロミドを用いた触媒.
- オーソ置換されたアリルアジドの反応.
- タンデム反応の中間物質と産物の分析.
主要な成果:
- アリルアジドから2,3-非置換インドールの合成に成功した.
- [1,2]-シフトによるタンデムエーテルC-H結合アミネーションの実証.
- [1,2]シフトコンポーネントの確立された好み: Me < 1° < 2° < Ph.
結論:
- 鉄(II) ブロミドはインドル形成の効果的な触媒である.
- タンデム反応は,置換されたインドールへの新しい経路を提供します.
- [1,2]シフトステップにおける移動能力は,電子的およびステリック的要因の影響を受けます.
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