Silver-Catalyzed Ring-Opening Strategy for the Synthesis of β- and γ-Fluorinated Ketones

被引：323

作者：

Zhao, Huijun ^{[1
]}

Fan, Xuefeng ^{[1
]}

Yu, Jiajia ^{[1
]}

Zhu, Chen ^{[1
,2
]}

机构：

[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Jiangsu, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 10期

基金：

中国国家自然科学基金;

关键词：

C-H FLUORINATION; COPPER-MEDIATED FLUORINATION; PHASE-TRANSFER CATALYST; ENANTIOSELECTIVE FLUORINATION; ARYL FLUORIDES; BOND FORMATION; BENZYLIC FLUORINATION; UNACTIVATED ALKENES; MEDICINAL CHEMISTRY; LATE-STAGE;

D O I：

10.1021/jacs.5b00939

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A regioselective synthesis of beta- and gamma-fluorinated ketones via silver-catalyzed ring opening is described. A variety of beta- and gamma-fluorinated ketones are efficiently prepared, respectively, from tertiary cyclopropanol and cyclobutanol precursors, providing a straightforward approach for the introduction of a fluorine atom into complex molecules. Preliminary mechanistic studies suggest that a radical-mediated sequential C-C bond cleavage and C-F bond formation pathway is involved.

引用

页码：3490 / 3493

页数：4

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