钯催化的共轭二烯的有氧分子间 1,2-二胺化：哌嗪和 2-哌嗪酮的区域和化学选择性合成。

Pd-Catalyzed Aerobic Intermolecular 1,2-Diamination of Conjugated Dienes: Regio- and Chemoselective Synthesis of Piperazines and 2-Piperazinones.

机构信息

Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, P. R. China.

Hunan Provincial Key Laboratory of Tumor Microenvironment Responsive Drug Research, Institute of Pharmacy & Pharmacology School of Pharmaceutical Science, Hengyang Medical School, University of South China, Hengyang, Hunan, 421001, P. R. China.

出版信息

Chemistry. 2022 Oct 12;28(57):e202201808. doi: 10.1002/chem.202201808. Epub 2022 Aug 22.

DOI:10.1002/chem.202201808

PMID:35916124

Abstract

Dinitrogen heterocycles are among the most important molecular structures, and the synthesis of these types of structures through intermolecular 1,2-diamination of olefins is a direct and efficient method. However, the types of nitrogen sources are mostly derived from ureas or arylamines, and nitrogen sources from aliphatic amines are still limited due to their distinct electronic and steric effects. Herein, we report a palladium-catalyzed aerobic intermolecular 1,2-diamination of conjugated dienes, using ethanediamine and α-amino amide derivatives as nitrogen sources respectively, for the synthesis of piperazines and 2-piperazinones in good yields (up to 95 %) and with high regio- and chemoselectivities.

摘要

二氮杂环化合物是最重要的分子结构之一，通过烯烃的分子间 1,2-二氨基化合成这些类型的结构是一种直接有效的方法。然而，氮源的类型大多来自于尿素或芳胺，由于脂肪族胺具有独特的电子和空间效应，其氮源仍然有限。在此，我们报道了钯催化的空气中共轭二烯的分子间 1,2-二氨基化反应，分别使用乙二胺和α-氨基酰胺衍生物作为氮源，以高产率（高达 95%）和高区域选择性和化学选择性合成哌嗪和 2-哌嗪酮。