Synthesis of spiro-1,2-dihydropyridine derivatives via cycloisomerization of 3-aza-1,5-enynes catalyzed by gold(I) complex/polyoxometalate hybrids

This study reports an optimized method for the synthesis of spiro-1,2-dihydropyridines via the cycloisomerization of 3-aza-1,5-enynes, catalyzed by heterogeneous gold(I)–polyoxometalate (POM) hybrids. By replacing traditional homogeneous catalysts with these hybrid systems, we achieved high yields (up to 82% isolated) in short reaction times, while minimizing product degradation. The reaction scope was demonstrated across a broad range of substrates, including aryl, alkyl, and heterocyclic derivatives, as well as variations in ring size and nitrogen substituents using 5 mol % of [Au I (IPr)(MeCN)][H 5 P 2 W 18 O 64 ] as catalyst.

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Publication Details

Journal
Beilstein Journal of Organic Chemistry
Published
2026-09-28
DOI
https://doi.org/10.3762/bjoc.22.106
Primary Topic
Catalytic Alkyne Reactions
Type
article
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article

Synthesis of spiro-1,2-dihydropyridine derivatives via cycloisomerization of 3-aza-1,5-enynes catalyzed by gold(I) complex/polyoxometalate hybrids

Pierre de Frémont, Aurélien Blanc, Stefan Chassaing, Fabian Schlimpen et al.
Beilstein Journal of Organic Chemistry
Catalytic Alkyne Reactions
article

Synthesis of spiro-1,2-dihydropyridine derivatives via cycloisomerization of 3-aza-1,5-enynes catalyzed by gold(I) complex/polyoxometalate hybrids

Pierre de Frémont, Aurélien Blanc, Stefan Chassaing, Fabian Schlimpen, Titien Simon
article en

Abstract

This study reports an optimized method for the synthesis of spiro-1,2-dihydropyridines via the cycloisomerization of 3-aza-1,5-enynes, catalyzed by heterogeneous gold(I)–polyoxometalate (POM) hybrids. By replacing traditional homogeneous catalysts with these hybrid systems, we achieved high yields (up to 82% isolated) in short reaction times, while minimizing product degradation. The reaction scope was demonstrated across a broad range of substrates, including aryl, alkyl, and heterocyclic derivatives, as well as variations in ring size and nitrogen substituents using 5 mol % of [Au I (IPr)(MeCN)][H 5 P 2 W 18 O 64 ] as catalyst.

Beilstein Journal of Organic ChemistryVol. 22
Openalex Percentile: Top 22%
Catalytic Alkyne Reactions
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