Silver-initiated radical ring expansion/fluorination of ethynyl cyclobutanols: efficient synthesis of monofluoroethenyl cyclopentanones

被引：35

作者：

Tian, Qingshan ^{[1
]}

Chen, Bin ^{[1
]}

Zhang, Guozhu ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

GREEN CHEMISTRY | 2016年 / 18卷 / 23期

关键词：

C BOND-CLEAVAGE; REGIOSELECTIVE SYNTHESIS; REGIOSPECIFIC SYNTHESIS; DIPEPTIDE ISOSTERES; FACILE SYNTHESIS; FLUORINATION; FLUOROALKENES; KETONES; ALKYL; OXIDATIONS;

D O I：

10.1039/c6gc02656g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A stereoselective synthesis of beta-halogenated 2-methylenecyclopentanones via silver-catalyzed formal ring expansion using water as the cosolvent is described. A variety of 2-methylenecyclopentanones with fluoro, chloro and bromo functionalities are efficiently prepared from 1-alkynyl cyclobutanols. This method offers facile access to halogenated complex molecules which are not only useful chemicals but also valuable building blocks for further derivatizations.

引用

页码：6236 / 6240

页数：5

共 5 条

[1] Synthesis of β-Selenylated Cyclopentanones via Photoredox-Catalyzed Selenylation/Ring-Expansion Cascades of Alkenyl Cyclobutanols
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[5] Two-Carbon Ring Expansion of Cyclobutanols to Cyclohexenones Enabled by Indole Radical Cation Intermediate: Development and Application to a Total Synthesis of Uleine
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