Copper-Catalyzed Carbonylative Cyclization of CO2: A Promising Approach for Synthesis of Flavone

被引：0

作者：

Huang, Zijun ^{[1
]}

Dong, Junyong ^{[1
]}

Liu, Pengtao ^{[1
]}

Yin, Yadi ^{[1
]}

Yi, Bing ^{[1
]}

Fang, Zhengjun ^{[1
]}

Jiang, Xiaolin ^{[2
]}

Li, Yuehui ^{[3
,4
]}

机构：

[1] Hunan Inst Engn, Coll Chem & Chem Engn, Hunan Prov Key Lab Environm Catalysis & Waste Rech, Xiangtan 411104, Peoples R China

[2] Shanghai Univ Med & Hlth Sci, Sch Pharm, Shanghai 201318, Peoples R China

[3] Shanghai Jiao Tong Univ, Coll Smart Energy, Shanghai 200240, Peoples R China

[4] Campus Res Excellence & Technol Enterprise CREATE, Carbon Negat Synthet Biol Biomat Prod CO2 CNSB, 1 CREATE Way, Singapore 138602, Singapore

来源：

ADVANCED SCIENCE | 2025年 / 12卷 / 13期

基金：

新加坡国家研究基金会; 中国国家自然科学基金;

关键词：

Carbon dioxide utilization; Carbonylation; CO2 mass transfer; Copper catalyst; Flavone; DERIVATIVES; ACETYLENES; ANNULATION; AURONES; ALKYNES; DBU;

D O I：

10.1002/advs.202415795

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Flavones are an important class of building blocks for numerous biologically active molecules, pharmaceuticals, and natural products. Reductive carbonylation of CO2 is a powerful method to provide high-value heterocycles quickly. However, examples of transition metal-catalyzed carbonylation to produce flavones using CO2 are quite scarce, and the related copper-catalyzed carbonylative cyclization of CO2 is not reported. Here, a general procedure is developed for the copper-catalyzed carbonylative C(sp3)-H bond synthesis of flavone using CO2 as the C1 source. Additionally, C-13-labeled flavones are successfully synthesized using [C-13]-CO2, demonstrating significant inhibitor activity against MCF-7 cells in antitumor assays. Mechanistic investigations suggest that the phenolic group accelerates CO2 mass transfer by promoting nucleophilic addition to DBU-CO(2 )complexes, followed by selective intramolecular carbonylative cyclization.

引用

页数：11

共 58 条

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