Palladium-catalyzed defluorinative alkynylation of polyfluoroalkyl ketones with alkynes for the synthesis of fluorinated fused furans

被引：14

作者：

Chu, Xue-Qiang ^{[1
]}

Zhi, Man-Ling ^{[1
]}

Zhang, Si-Xuan ^{[1
]}

Wang, Ya-Wen ^{[1
]}

Rao, Weidong ^{[2
]}

Xu, Haiyan ^{[3
]}

Shen, Zhi-Liang ^{[1
]}

机构：

[1] Nanjing Tech Univ, Tech Inst Fluorochem TIF, Inst Adv Synth, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China

[2] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Prov Key Lab Chem & Utilizat Agroforest B, Nanjing 210037, Peoples R China

[3] Jiangsu Univ Sci & Technol, Sch Environm & Chem Engn, Zhenjiang 212003, Jiangsu, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2021年 / 8卷 / 03期

基金：

中国国家自然科学基金;

关键词：

Catalysis - Palladium compounds - Organic pollutants - Palladium - Aromatic compounds - Hydrocarbons;

D O I：

10.1039/d0qo01009j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Pd-catalyzed C-F bond alkynylation of polyfluoroalkyl ketones with terminal alkynes has been developed. The method gives access to a range of modular perfluoroalkyl- and alkynyl-substituted furan derivatives in moderate yields with high chemoselectivity and regioselectivity. The key to the success of the present cascade reaction mainly relies on the well-controlled sequence of functionalization and alkynylation of multiple C(sp(3))-F bonds. Mechanistic studies showed that the reaction presumably proceeded through a chelation-assisted oxidative addition of Pd to the C-F bond.

引用

页码：572 / 578

页数：7

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