C70複合と無銅トリプルクリック反応によるアルキンメタテシスによるサイクロパフェニレンアセチレン合成
Semin Lee1, Etienne Chénard1, Danielle L Gray1
1Beckman Institute for Advanced Science and Technology, ‡Department of Chemistry, ∥School of Chemical Sciences, University of Illinois at Urbana-Champaign , Urbana, Illinois 61801, United States.
Journal of the American Chemical Society
|October 11, 2016
まとめ
アルキンメタテシスは,サイクロパフェニルエセチレン誘導体を効率的に合成した. このマクロサイクルはC70フルレンと緊密に結合し,銅のないサイクル添加反応を容易にした.
科学分野:
- 有機化学
- 超分子化学
- 材料科学
背景:
- マクロサイクル化合物は,分子認識とカプセル化のための超分子化学において極めて重要です.
- サイクロパフェニレンは,ユニークな電子および構造特性を有するマクロサイクルの一種です.
- フラーレンの封装は,新しい材料を開発し,宿主-ゲストの相互作用を研究するために興味があります.
研究 の 目的:
- サイクロペニルエセチレン誘導体の効率的な合成経路を開発する.
- これらのマクロサイクルの宿主-ゲスト複合性をC70フルレンで調べる.
- マクロサイクルにおけるストレントアルキンの反応性を調べる.
主な方法:
- マクロサイクリングのためのアルキンの転移.
- 特徴づけのためのスペクトロスコピクと結晶学的技術.
- C70封入を評価するための拘束力のある研究
- 銅のないアジド-アルキンのサイクル添加反応.
主要な成果:
- アルキンメタテシスによるサイクロパフェニルエセチレン誘導体の高産量合成
- マクロサイクルの空洞内でのC70の緊密な結合を,誘導的フィットメカニズムによって実証する.
- 50 °Cで成功した銅のない3倍アジドアルキンのサイクル添加.
結論:
- アルキンメタテシスは,機能的なサイクロパフェニルエセチレンマクロサイクルを構成する効果的な戦略である.
- 合成されたマクロサイクルは,C70フルレンの選択的および強力な結合を示す.
- ストレインされたアルキンは,温和で銅のない条件下で効率的なクリック化学に適しています.
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