Convergent Synthesis of Polysubstituted Furans via Catalytic Phosphine Mediated Multicomponent Reactions

Xia Fan; Rongshun Chen; Jie Han; Zhengjie He

doi:10.3390/molecules24244595

Convergent Synthesis of Polysubstituted Furans via Catalytic Phosphine Mediated Multicomponent Reactions

Molecules. 2019 Dec 16;24(24):4595. doi: 10.3390/molecules24244595.

Authors

Xia Fan¹, Rongshun Chen², Jie Han¹, Zhengjie He¹

Affiliations

¹ The State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
² Jiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China.

Abstract

Tri- or tetrasubstituted furans have been prepared from terminal activated olefins and acyl chlorides or anhydrides by a multicomponental convergent synthesis mode. Instead of stoichiometric nBu₃P, only catalytic nBu₃P or nBu₃P=O is needed to furnish the furans in modest to excellent yields with a good functional group tolerance under the aid of reducing agent silane. This synthetic method features a silane-driven catalytic intramolecular Wittig reaction as a key annulation step and represents the first successful application of catalytic Wittig reaction in multicomponent cascade reaction.

Keywords: catalytic Wittig reaction; multicomponent reaction; phosphine oxides; polysubstituted furans; silanes.

MeSH terms

Catalysis
Chemistry Techniques, Synthetic*
Furans / chemical synthesis*
Furans / chemistry
Molecular Structure
Phosphines / chemistry*

Substances

Furans
Phosphines
phosphine

Abstract

MeSH terms

Substances

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