トリアルキラミンN-CH3グループの選択C-H機能化における反熱力学的水素原子抽象
Joshua P Barham1,2, Matthew P John2, John A Murphy1
1WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde , 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.
Journal of the American Chemical Society
|November 5, 2016
まとめ
この研究は,アミンのN-メチル群を選択的に機能させるための新しい1ポット法を導入する. この化学的変換により,薬剤を含む複雑な分子の効率的な部位選択的改変が可能になります.
科学分野:
- 有機化学
- カタリシス
- 合成方法論
背景:
- アミンのC−H結合の選択的機能化は,有機合成における重要な課題である.
- 既存の方法は,他のアルキル置換剤よりもN-メチル群の選択性が欠けていることが多い.
研究 の 目的:
- N-メチル-N,N-ダイアキラミンのN-メチル群の機能化のための高度に選択的で効率的なプロトコルを開発する.
- 複雑な分子の末期機能化におけるこの方法の有用性を実証する.
主な方法:
- トライアリアルミニウム塩による酸化により,インシットで生成されたラジカルカチオン DABCO•+ (1,4-ディアザビサイクロ[2.2.2]オクタンラジカルカチオン) を利用したワンポットプロトコル.
- N-CH3群から選択的にC-Hを抽出し,その後に有機金属核性分子と反応する.
主要な成果:
- N-CH2RまたはN-CHR2グループに対するN-CH3機能化の高い化学選択性を達成した.
- 試料のスケーラビリティとリサイクル可能性が証明されている.
- 自然製品や医薬品の機能化に成功しました
結論:
- 開発されたプロトコルは,N-メチル群の承認のための新しい高度に選択的な経路を提供します.
- この方法は,薬剤発見と天然製品化学における迅速な誘導とSAR研究のための強力なツールを提供します.
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