Copper-Promoted Coupling of Carbon Dioxide and Propargylic Alcohols: Expansion of Substrate Scope and Trapping of Vinyl Copper Intermediate

被引：68

作者：

Ouyang, Lu ^{[1
]}

Tang, Xiaodong ^{[1
]}

He, Haitao ^{[1
]}

Qi, Chaorong ^{[1
]}

Xiong, Wenfang ^{[1
]}

Ren, Yanwei ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 11期

基金：

中国国家自然科学基金;

关键词：

carbon dioxide fixation; copper; cyclic carbonate; propargylic alcohols; vinyl copper intermediate; ALKYLIDENE CYCLIC CARBONATES; BETA-OXOPROPYL CARBONATES; EFFICIENT SYNTHESIS; CUPROUS CHLORIDE; CO2; FIXATION; TRANSFORMATION; ACTIVATION; CATALYST; CYCLIZATION; PALLADIUM;

D O I：

10.1002/adsc.201500088

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We have successfully demonstrated that in the presence of N,N-diisopropylethylamine, copper iodide could efficiently catalyze the coupling of internal propargylic alcohols with carbon dioxide to afford the corresponding -alkylidene cyclic carbonates in moderate to excellent yields. Moreover, we have developed a new and versatile protocol for the chemo- and stereoselective synthesis of a wide range of (E)--iodoalkylidene cyclic carbonates from carbon dioxide, propargylic alcohols and potassium iodide using copper salt as the promoter. The process is proposed to proceed through the trapping of the vinyl copper intermediate by in situ generated triiodide ion as electrophile.

引用

页码：2556 / 2565

页数：10

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