Copper-Catalyzed Fluoroolefination of Silyl Enol Ethers and Ketones toward the Synthesis of β-Fluoroenones

被引：47

作者：

Li, Yanlin ^{[1
]}

Liu, Jing ^{[1
]}

Zhao, Shuang ^{[1
]}

Du, Xuzhao ^{[1
]}

Guo, Minjie ^{[2
]}

Zhao, Wentao ^{[1
]}

Tang, Xiangyang ^{[1
]}

Wang, Guangwei ^{[1
]}

机构：

[1] Tianjin Univ, Sch Sci, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China

[2] Tianjin Univ, Inst Mol Design & Synth, Hlth & Sci Platform, Tianjin 300072, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 04期

关键词：

FLUORINATED BUILDING-BLOCK; HECK-TYPE REACTION; ALPHA-FLUOROENONES; STEREOSELECTIVE-SYNTHESIS; ARYLBORONIC ACIDS; COUPLING REACTION; CARBOXYLIC-ACIDS; HIGHLY EFFICIENT; AQUEOUS-MEDIA; ALKENES;

D O I：

10.1021/acs.orglett.7b03700

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and facile synthetic method for beta-fluoroenones from silyl enol ethers or ketones, with a copper-amine catalyst system, has been developed. The reaction proceeded by a tandem process of difluoroalkylation-hydrolysis-dehydro-fluorination. This method is characterized by high yields, excellent Z/E ratios, a low-cost catalyst, and a broad substrate scope. The synthetic potential of beta-fluoroenones has been demonstrated by the construction of various complicated organofluorine molecules.

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页码：917 / 920

页数：4

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