Tandem S-N(2)' nucleophilic substitution/oxidative radical cyclization of aryl substituted allylic alcohols with 1,3-dicarbonyl compounds
Tandem S-N(2)' nucleophilic substitution/oxidative radical cyclization of aryl substituted allylic alcohols with 1,3-dicarbonyl compounds
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DOI：
10.1039/c7ob00620a
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发表时间：
2017
影响因子：
3.2
通讯作者：
Zhang Xiao-Ming
中科院分区：
文献类型：
--
作者：
Zhang Zhen;Li Cheng;Wang Shao-Hua;Zhang Fu-Min;Han Xue;Tu Yong-Qiang;Zhang Xiao-Ming
以Mn（OAc）3为氧化剂，芳基取代烯丙醇与1，3-二羰基化合物发生SN 2 ′亲核取代/氧化自由基环化串联反应，快速合成了多取代二氢呋喃（DHF）衍生物.使用弱酸性的六氟异丙醇（HFIP）作为溶剂，而不是AcOH，成功地提高了产率，扩大了这种类型的自由基环化反应的底物范围。机理研究证实了级联反应过程涉及最终的自由基环化。
A novel and efficient tandem SN2′ nucleophilic substitution/oxidative radical cyclization reaction of aryl substituted allylic alcohols with 1,3-dicarbonyl compounds has been developed by using Mn(OAc)3 as an oxidant, which enables the expeditious synthesis of polysubstituted dihydrofuran (DHF) derivatives in moderate to high yields. The use of weakly acidic hexafluoroisopropanol (HFIP) as the solvent rather than AcOH has successfully improved the yields and expanded the substrate scope of this type of radical cyclization reactions. Mechanistic studies confirmed the cascade reaction process involving a final radical cyclization.