Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols

被引：59

作者：

Arimitsu, Satoru ^{[1
]}

Jacobsen, Jesse M. ^{[1
]}

Hammond, Gerald B. ^{[1
]}

机构：

[1] Univ Louisville, Dept Chem, Louisville, KY 40292 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 07期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1021/jo800088y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The iodocyclization of gem-difluorohomoallenyl and gem-difluorohomopropargyl alcohols with I-2 and ICI, respectively, produced the corresponding,fluorinated iodofuran analogues in good yields. The iodo substituent in fluorinated 4-iodofurans was utilized as a synthetic handle to prepare multisubstituted 3-fluorofurans using a Suzuki cross-coupling reaction. The yields of both iodocyclization of gem-difluorohomopropargyl alcohol and subsequent Suzuki coupling were dramatically enhanced by microwave irradiation.

引用

页码：2886 / 2889

页数：4

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