Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols
Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols
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DOI：
10.1021/jo800088y
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发表时间：
2008-04-04
影响因子：
3.6
通讯作者：
Hammond, Gerald B.
中科院分区：
文献类型：
--
作者：
Arimitsu, Satoru;Jacobsen, Jesse M.;Hammond, Gerald B.
偕二氟高丙二烯醇和偕二氟高丙炔醇分别用 I-2 和 ICI 进行碘环化，以良好的产率产生相应的氟化碘呋喃类似物。利用氟化4-碘呋喃中的碘取代基作为合成柄，通过Suzuki交叉偶联反应制备多取代的3-氟呋喃。微波辐射显着提高了偕二氟高炔丙醇的碘环化反应和随后的 Suzuki 偶联反应的产率。
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.