サルフォナミドとオレフィンとのC-H→C-Nクロスカップリング
1Roger Adams Laboratory, Department of Chemistry , University of Illinois , Urbana , Illinois 61801 , United States.
Journal of the American Chemical Society
|February 13, 2018
まとめ
この研究は,アリルアミンを生成するための新しいC-Hアミナ法を導入しています. 硫黄酸-オキサゾリン (SOX) リガンドによるパラジウム触媒は,オレフィンとアミンの効率的な結合を可能にし,合成化学を進める.
科学分野:
- 有機化学
- カタリシス
- 合成方法論
背景:
- 窒素-炭素結合の形成は化学合成において極めて重要です.
- C-N カップリングの既存の方法は,しばしば機能化された基板を必要とします.
- 直接的なC-H機能化は,より原子経済的なアプローチを提供します.
研究 の 目的:
- C ((sp3) -N 断片結合のための新しい触媒方法を開発する.
- 末端オレフィンとアミンの分子間アリルC-Hアミナ化を達成する.
- この変換におけるパラジウム/硫酸化オクサゾリン (SOX) 触媒の有用性を調査する.
主な方法:
- パラジウム (II) 触媒と硫化酸化オクサゾリン (SOX) リガンドを併用した.
- N-トリフリルで保護されたアリファティック・アロマティック・アミンをカップリングパートナーとして使用した.
- 断片結合条件下で末端オレフィンとの反応を調査した.
主要な成果:
- 56種類のアリルアミンを 合成しました
- 平均75%の高い収穫率を達成した.
- 線形:分岐性で>20:1の平均比率とE:Z同位体で>20:1の平均比率で,優れた地域とステレオ選択性を示した.
- 機理学的な研究では,カチオン型π-アリルパラジウム中間体をサポートするSOXリガンドの役割が示された.
結論:
- 新しい Pd (II) /SOX触媒による分子間アリルC-Hアミネーション反応を確立した.
- この方法は,高い選択性を持つ有価なアリルアミン製品への効率的なアクセスを提供します.
- この発見は,SOXリガンドがC-N結合形成を容易にする可能性を強調しています.
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