Palladium-Catalyzed C-C Coupling of Aryl Halides with Isocyanides: An Alternative Method for the Stereoselective Synthesis of (3E)-(Imino)isoindolin-1-ones and (3E)-(Imino)thiaisoindoline 1,1-Dioxides

被引：57

作者：

Liu, Bifu ^{[1
]}

Li, Yibiao ^{[1
]}

Jiang, Huanfeng ^{[1
]}

Yin, Meizhou ^{[1
]}

Huang, Huawen ^{[1
]}

机构：

[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 11-12期

基金：

中国国家自然科学基金;

关键词：

C-C coupling; isocyanides; nitrogen-containing heterocycles; one-pot cyclization; palladium-catalyzed reaction; SINGLE-STEP SYNTHESIS; MULTICOMPONENT REACTIONS; OLIGOSUBSTITUTED PYRROLES; REGIOSELECTIVE SYNTHESIS; 3-COMPONENT REACTION; C(SP(3))-H BONDS; DIRECT ACCESS; CHEMISTRY; CARBONYLATION; HETEROCYCLES;

D O I：

10.1002/adsc.201200212

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A palladium-catalyzed, one-pot cyclization reaction to construct (3E)-(imino)isoindolin-1-ones and (3E)-(imino)thiaisoindoline 1,1-dioxides by introducing ortho-reactive functional groups on aryl halides is reported. Under optimal conditions, the cyclization reaction afforded the corresponding products in good to excellent yields (up to 93%) with high stereoselectivity. Notably, this transformation successfully extends its application for the synthesis of phenanthridines and dibenzooxazepines. This new synthetic protocol not only extends the application platform for palladium-catalyzed C-C coupling of aryl halides with isocyanides,but also opens atom-economic and step-economic synthetic routes for nitrogen-containing heterocyclic compounds with wide functional group compatibility.

引用

页码：2288 / 2300

页数：13

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