Si-P,Si-S,Si-N,およびC-C結合にアリンを挿入するための新しい阻害アミド基
Milad Mesgar1, Justin Nguyen-Le1, Olafs Daugulis1
1Department of Chemistry , University of Houston , Houston , Texas 77204-5003 , United States.
Journal of the American Chemical Society
|October 24, 2018
まとめ
新しい阻害されたリチウムアミド基は,Si-P,Si-S,Si-N,およびC-Cを含む様々な結合にアリンを効率的に挿入することを可能にします. この方法はアンスラセンのような複雑な分子に 汎用的な1段階合成を提供します
科学分野:
- 有機化学
- 有機金属化学
背景:
- 複雑な有機分子を合成するのに不可欠です.
- アリンの反応性を制御する新しい反応剤の開発は,合成の進歩にとって不可欠です.
研究 の 目的:
- 新しい阻害されたリチウムアミド基,リチウムダイアマンチラミド (LDAM) を導入する.
- LDAMがアリン挿入反応を促進する有用性を実証する.
- アントラセンの1段階合成を開発する.
主な方法:
- アリルトリフラートとハリドからアリンが生成された.
- 生成されたアリンは,シライライテッド・フォスフィン,硫化物,およびアミンとの挿入反応を受けた.
- アリルハリドとケトンを用いて,アントラセンの1段階合成を達成した.
主要な成果:
- LDAMを使用して,Si-P,Si-S,Si-N,およびC-C結合にアリンを効率的に挿入することが達成されました.
- LDAMベースは,リチウムテトラメチルパイペリド (LiTMP) と比較して,より高い収量を提供しました.
- シアノ,アリル,アルキル,ホルミルを含む様々な機能群は,反応条件と相容れていました.
結論:
- LDAMは,アリン挿入反応のための非常に効果的なベースです.
- LDAMの体積は,ベースとの副作用を最小限に抑え,制限反応剤として使用できます.
- この方法論は多様な有機構造を 構築するための強力なツールです
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