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Issue 15, 2017
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Tandem SN2′ nucleophilic substitution/oxidative radical cyclization of aryl substituted allylic alcohols with 1,3-dicarbonyl compounds

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Abstract

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.

Graphical abstract: Tandem SN2′ nucleophilic substitution/oxidative radical cyclization of aryl substituted allylic alcohols with 1,3-dicarbonyl compounds

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Publication details

The article was received on 13 Mar 2017, accepted on 17 Mar 2017 and first published on 17 Mar 2017


Article type: Paper
DOI: 10.1039/C7OB00620A
Citation: Org. Biomol. Chem., 2017,15, 3239-3247
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    Tandem SN2′ nucleophilic substitution/oxidative radical cyclization of aryl substituted allylic alcohols with 1,3-dicarbonyl compounds

    Z. Zhang, C. Li, S. Wang, F. Zhang, X. Han, Y. Tu and X. Zhang, Org. Biomol. Chem., 2017, 15, 3239
    DOI: 10.1039/C7OB00620A

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