Unexpected Base-Promoted Synthesis of Tetrasubstituted Furans via Palladium-Catalyzed Oxidation and Cyclization of Carbon-Carbon Triple Bond with Molecular Oxygen

A new approach to the synthesis of tetrasubstituted furans using aromatic alkynes catalyzed by PdCl2 in DMA (N,N-dimethylacetamide)-H2O with dioxygen as the sole oxidant is described, in which the oxygen atom of the furan was from water. The preliminary mechanistic understanding of this transformati...

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Bibliographic Details
Published inSynlett no. 7; pp. 1074 - 1078
Main Authors Wang, Lianyue, Li, Jun, Lv, Ying, Zhao, Gongda, Gao, Shuang
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.04.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TRANSFORMATION
KETONES
HETEROCYCLES
RINGS
furans
alkynes
oxidation
EFFICIENT SYNTHESIS
palladium
CYCLOISOMERIZATION
SYSTEMS
molecular oxygen
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Summary:A new approach to the synthesis of tetrasubstituted furans using aromatic alkynes catalyzed by PdCl2 in DMA (N,N-dimethylacetamide)-H2O with dioxygen as the sole oxidant is described, in which the oxygen atom of the furan was from water. The preliminary mechanistic understanding of this transformation was investigated.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0031-1290526