Controlled gold-catalyzed 5- <i>exo-dig</i> cyclization of 3-sulfur-substituted 1,3-dien-5-ynes for synthesizing fulvenes and the <i>in situ</i> reaction with indoles

Densely substituted fulvenes have been synthesized from 1,3-dien-5-ynes by gold-catalyzed 5-<i>exo-dig</i> cyclization, determined by the S-substituent. In addition, these fulvenes interact with the gold catalyst, forming fulvenium intermediates that react with indoles in a one-pot two-step protocol to synthesize 3-(alkylidene-cyclopent-2-en-1-yl)-1<i>H</i>-indoles, by the cooperative action of gold and Brønsted acid catalysts.

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Publication Details

Journal
Chemical Communications
Published
2025-12-22
DOI
https://doi.org/10.1039/d5cc06478c
Primary Topic
Catalytic Alkyne Reactions
Type
article
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article

Controlled gold-catalyzed 5- exo-dig cyclization of 3-sulfur-substituted 1,3-dien-5-ynes for synthesizing fulvenes and the in situ reaction with indoles

Samuel Suárez‐Pantiga, Carlos Arribas-Torrecilla, Roberto Sanz, Clara Martínez-Núñez
Chemical Communications
Catalytic Alkyne Reactions
article

Controlled gold-catalyzed 5- exo-dig cyclization of 3-sulfur-substituted 1,3-dien-5-ynes for synthesizing fulvenes and the in situ reaction with indoles

Samuel Suárez‐Pantiga, Carlos Arribas-Torrecilla, Roberto Sanz, Clara Martínez-Núñez
article en

Abstract

Densely substituted fulvenes have been synthesized from 1,3-dien-5-ynes by gold-catalyzed 5-<i>exo-dig</i> cyclization, determined by the S-substituent. In addition, these fulvenes interact with the gold catalyst, forming fulvenium intermediates that react with indoles in a one-pot two-step protocol to synthesize 3-(alkylidene-cyclopent-2-en-1-yl)-1<i>H</i>-indoles, by the cooperative action of gold and Brønsted acid catalysts.

Chemical CommunicationsVol. 62(7)
Universidad de Burgos (ES)
Openalex Percentile: Top 34%
Catalytic Alkyne Reactions
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Controlled gold-catalyzed 5- <i>exo-dig</i> cyclization of 3-sulfur-substituted 1,3-dien-5-ynes for synthesizing fulvenes and the <i>in situ</i> reaction with indoles — Samuel Suárez‐Pantiga, Carlos Arribas-Torrecilla, et al. · Chemical Communications (2025) | TGRS Research Map | TGRS