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钯催化氧化串联氮杂瓦克/赫克环化反应构建稠合5,6-双环氮、氧杂环化合物

Pd -Catalyzed Oxidative Tandem aza-Wacker/Heck Cyclization for the Construction of Fused 5,6-Bicyclic N,O-Heterocycles.

作者信息

Ye Chenghao, Kou Xuezhen, Xia Jingzhao, Yang Guoqiang, Kong Li, Wei Quhao, Zhang Wanbin

机构信息

Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, China.

6th People's Hospital South Campus, Shanghai Jiao Tong University, 6600 Nanfeng Hwy, Shanghai, 200233, China.

出版信息

Chem Asian J. 2018 May 30. doi: 10.1002/asia.201800646.

DOI:10.1002/asia.201800646
PMID:29851272
Abstract

A Pd -catalyzed oxidative tandem cyclization was developed for the construction of fused 5,6-bicyclic N, O-heterocycles. This reaction was enabled by the combined use of a 3-methylpyridine ligand and pentafluorobenzoic acid additive. A range of heterocyclic products with different substituents could be prepared in moderate to good yields via this methodology. Several transformations, including a scaled-up preparation of product 2 a, were also carried out showing the good applicability of our methodology.

摘要

开发了一种钯催化的氧化串联环化反应来构建稠合的5,6-双环N,O-杂环。该反应通过3-甲基吡啶配体和五氟苯甲酸添加剂的联合使用得以实现。通过该方法可以以中等至良好的产率制备一系列具有不同取代基的杂环产物。还进行了几种转化反应,包括产物2a的放大制备,展示了我们方法的良好适用性。

相似文献

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Pd -Catalyzed Oxidative Tandem aza-Wacker/Heck Cyclization for the Construction of Fused 5,6-Bicyclic N,O-Heterocycles.钯催化氧化串联氮杂瓦克/赫克环化反应构建稠合5,6-双环氮、氧杂环化合物
Chem Asian J. 2018 May 30. doi: 10.1002/asia.201800646.
2
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引用本文的文献

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Palladium-catalyzed cascade of aza-Wacker and Povarov reactions of aryl amines and 1,6-dienes for hexahydro-cyclopenta[b]quinoline framework.钯催化芳基胺与1,6-二烯的氮杂瓦克反应和波瓦罗夫反应串联构建六氢环戊并[b]喹啉骨架。
Nat Commun. 2024 Aug 8;15(1):6776. doi: 10.1038/s41467-024-51173-4.
2
Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles.钯催化乙烯基环丙烷甲酰胺的分子内氮杂瓦克型环化反应,以制备构象受限的氮杂[3.1.0]双环化合物。
RSC Adv. 2023 Sep 11;13(39):27158-27166. doi: 10.1039/d3ra05440c. eCollection 2023 Sep 8.