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sp3 carbon–fluorine bond activation in 2,2-difluorohomoallylic alcohols via nucleophilic 5-endo-trig cyclisation: synthesis of 3-fluorinated furan derivatives†
Chemical Communications ( IF 4.9 ) Pub Date : 2018-09-25 00:00:00 , DOI: 10.1039/c8cc04643c
Takeshi Fujita 1, 2, 3, 4, 5 , Ryutaro Morioka 1, 2, 3, 4, 5 , Tomohiro Arita 1, 2, 3, 4, 5 , Junji Ichikawa 1, 2, 3, 4, 5
Affiliation  

Nucleophilic 5-endo-trig cyclisation was achieved in 2,2-difluorohomoallylic alcohols. Upon treatment with potassium hydride, 2,2-difluorohomoallylic alcohols underwent an intramolecular SN2′-type reaction to afford 3-fluoro-2,5-dihydrofurans in high yields. In addition, the oxidation of these dihydrofurans formed 4-fluorofuran-2(5H)-ones. Thus, ring-fluorinated furan derivatives were efficiently obtained via allylic sp3 carbon–fluorine bond cleavage.

中文翻译:

通过亲核的5-内-trig环化作用使2,2-二氟同烯丙基醇中的 sp 3碳-氟键活化:3-氟代呋喃衍生物的合成

在2,2-二氟均烯丙基醇中实现了亲核性5-内-trig环化。在用氢化钾处理,2,2- difluorohomoallylic醇进行分子内小号Ñ 2'-型反应,得到3-氟-2,5-二氢呋喃高收率。此外,这些二氢呋喃的氧化形成了4-氟呋喃-2(5 H)-one 。因此,通过烯丙基sp 3碳-氟键裂解可有效获得环氟化呋喃衍生物。
更新日期:2018-09-25
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