Suzuki Hirotsugu, Moro Ryota, Matsuda Takanori
Tenure-Track Program for Innovative Research, University of Fukui, 3-9-1 Bunkyo, Fukui-shi, Fukui 910-8507, Japan.
Department of Applied Chemistry, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.
J Am Chem Soc. 2024 May 22;146(20):13697-13702. doi: 10.1021/jacs.4c00841. Epub 2024 May 14.
This paper reports a direct α-(hetero)arylation of acrylamides through an inverse electron-demand nucleophilic addition, specifically an -Michael-type addition. The introduction of a quinolyl directing group facilitates the nucleophilic addition of (hetero)arenes to the α-position of acrylamides. The quinolyl directing group effectively suppresses undesired β-hydrogen elimination and is removable for subsequent derivatization. The presented method provides an atom economical synthesis of α-(hetero)arylamide with a high degree of functional group tolerance.
本文报道了通过逆电子需求亲核加成反应，特别是迈克尔型加成反应，实现丙烯酰胺的直接α-（杂）芳基化反应。喹啉导向基团的引入促进了（杂）芳烃对丙烯酰胺α位的亲核加成。喹啉导向基团有效地抑制了不期望的β-氢消除反应，并且可用于后续衍生化反应而被去除。所提出的方法提供了一种原子经济性的α-（杂）芳基酰胺合成方法，具有高度的官能团耐受性。
