Palladium-Catalyzed Bromoalkynylation of C-C Double Bonds: Ring-Structure-Dependent Synthesis of 7-Alkynyl Norbornanes and Cyclobutenyl Halides

被引：105

作者：

Li, Yibiao ^{[1
]}

Liu, Xiaohang ^{[1
]}

Jiang, Huanfeng ^{[1
]}

Liu, Bifu ^{[1
]}

Chen, Zhengwang ^{[1
]}

Zhou, Peng ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 28期

基金：

中国国家自然科学基金;

关键词：

bromoalkynylation; cycloaddition; norbornanes; palladium; rearrangement; ENANTIOSELECTIVE 2+2 CYCLOADDITION; REDUCTIVE ELIMINATION; BICYCLIC ALKENES; OPENING REACTIONS; ARYL IODIDES; COMPLEXES; REACTIVITY; EFFICIENT; ALKYNES; LIGAND;

D O I：

10.1002/anie.201100002

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Strain versus flexibility: The palladium-catalyzed reaction of haloalkynes with norbornene derivatives leads to 7-alkynyl norbornane products (see scheme). Key to the success of this reaction is the formation of a "bridging" palladium species, which can rearrange to result in a C-7 functionalization. The ring-structure-dependent [2+2] cycloaddition of haloalkynes with cyclooctene has been achieved in moderate to good yields under similar conditions. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：6341 / 6345

页数：5

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