Gold(I)‐Catalyzed Synthesis of Benzofurans from Tetrahydropyranyl (THP) Ethers of <i>o</i>‐Alkynylphenols

The activation of π-systems in alkenes and alkynes by homogeneous gold catalysts is a powerful tool for the synthesis of benzo-fused heterocycles. Decades of development in the area of gold catalysis have brought an array of new catalysts and with them the discovery of new modes of carbophilic activation of π-systems in alkenes and alkynes, and investigations of previously unknown mechanistic pathways. In alignment with these efforts, we report a cyclization of tetrahydropyranyl ethers of 2-alkynylphenols to form benzofurans catalyzed by a gold(I)-NHC complex. The reaction proceeds efficiently at very low catalyst loadings, and the products form in good yields.

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Publication Details

Journal
Chemistry - An Asian Journal
Published
2025-05-09
DOI
https://doi.org/10.1002/asia.202500093
Primary Topic
Catalytic Alkyne Reactions
Type
article
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article

Gold(I)‐Catalyzed Synthesis of Benzofurans from Tetrahydropyranyl (THP) Ethers of o‐Alkynylphenols

Jeremy W. Pisor, Isabella Garcia, Hubert Muchalski, Kirubel Mamo
Chemistry - An Asian Journal
Catalytic Alkyne Reactions
article

Gold(I)‐Catalyzed Synthesis of Benzofurans from Tetrahydropyranyl (THP) Ethers of o‐Alkynylphenols

Jeremy W. Pisor, Isabella Garcia, Hubert Muchalski, Kirubel Mamo
article en

Abstract

The activation of π-systems in alkenes and alkynes by homogeneous gold catalysts is a powerful tool for the synthesis of benzo-fused heterocycles. Decades of development in the area of gold catalysis have brought an array of new catalysts and with them the discovery of new modes of carbophilic activation of π-systems in alkenes and alkynes, and investigations of previously unknown mechanistic pathways. In alignment with these efforts, we report a cyclization of tetrahydropyranyl ethers of 2-alkynylphenols to form benzofurans catalyzed by a gold(I)-NHC complex. The reaction proceeds efficiently at very low catalyst loadings, and the products form in good yields.

Chemistry - An Asian JournalVol. 20(12)
University of California, Santa Barbara (US), California State University, Fresno (US)
Openalex Percentile: Top 93%
Catalytic Alkyne Reactions
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