Palladium-catalyzed cascade carboesterification of norbornene with alkynes

被引：7

作者：

Wu, Wanqing ^{[1
,2
]}

Li, Can ^{[2
]}

Li, Jianxiao ^{[2
]}

Jiang, Huanfeng ^{[2
]}

机构：

[1] South China Univ Technol, State Key Lab Luminescent Mat & Devices, Guangzhou 510640, Guangdong, Peoples R China

[2] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Guangdong, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 44期

基金：

中国国家自然科学基金;

关键词：

METHYLENE-GAMMA-LACTONES; STEREOSELECTIVE-SYNTHESIS; IONIC LIQUIDS; ANNULATION; CYCLIZATION; ALKENES; ACCESS; DERIVATIVES; 1,6-ENYNES; CARBONYLATION;

D O I：

10.1039/c8ob01799a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and convenient palladium-catalyzed cascade carboesterification of norbornenes (NBE) with alkynes has been accomplished to afford functionalized alpha-methylene gamma-lactone and tetrahydrofuran derivatives in good to excellent yields. This new strategy exhibits excellent atom- and step-economy, good functional group tolerance and broad substrate scope. In particular, NBE-palladium species was proposed to be the key intermediate in the catalytic cycle to suppress the beta-H elimination process. Notably, the developed protocol provides a straightforward and practical tool for the construction of diverse oxygen-containing heterocycle frameworks, illustrating a promising application in synthetic and pharmaceutical chemistry.

引用

页码：8495 / 8504

页数：10

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