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钯催化串联一锅法通过顺序 Heck 和氧化胺化反应合成π扩展咪唑。

Palladium-catalyzed tandem one-pot synthesis of π-expanded imidazoles through a sequential Heck and oxidative amination reaction.

机构信息

Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin, 150040, P. R. China.

出版信息

Org Biomol Chem. 2019 Apr 17;17(16):4014-4023. doi: 10.1039/c9ob00482c.

DOI:10.1039/c9ob00482c
PMID:30949653
Abstract

An efficient palladium-catalyzed route for tandem synthesis of imidazole-fused polyheterocycles from 2-vinyl imidazoles and aryl halides is described. The sequentially accomplished process comprises intermolecular Heck arylation of 2-vinyl imidazoles followed by an intramolecular aerobic oxidative C-H amination reaction promoted by the same Pd catalyst. This Pd-catalyzed tandem approach offers a straightforward protocol for the assembly of benzimidazo/phenanthroimidazo[1,2-a]quinolines in moderate to high yields, serving as a useful tool for the discovery of fluorescent materials.

摘要

本文描述了一种从 2-乙烯基咪唑和芳基卤化物出发,经钯催化串联合成咪唑稠合多杂环的有效方法。该串联过程依次包括 2-乙烯基咪唑的分子间 Heck 芳基化反应,以及在相同的钯催化剂作用下,通过分子内有氧氧化 C-H 胺化反应。该钯催化的串联方法为苯并咪唑/菲并咪唑[1,2-a]喹啉的构建提供了一种直接的方法,在中等至较高产率下得到目标产物,可作为发现荧光材料的有用工具。

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