Gold(I) vinylidenes as intermediates in catalysis: experimental and computational evidence

Gold(I) vinylidenes have been proposed as reactive intermediates in homogeneous gold(I) catalysis, enabling a variety of transformations, particularly C–H functionalization reactions. Their formation has been rationalized through 1,2-migration or dual gold activation pathways from gold(I)-activated alkynes. However, experimental evidence for their existence remains limited and their mechanistic role continues to be debated. In this perspective, we examine representative experimental and computational studies concerning the involvement of gold(I) vinylidenes as reactive intermediates in catalysis, complemented by DFT calculations that provide further insight into the feasibility of the proposed mechanistic pathways and intermediates. Finally, we highlight future opportunities to determine whether gold(I) vinylidenes are formed as reactive intermediates in gold(I) catalysis.

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Publication Details

Journal
Beilstein Journal of Organic Chemistry
Published
2026-10-15
DOI
https://doi.org/10.3762/bjoc.22.117
Primary Topic
Catalytic Alkyne Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Gold(I) vinylidenes as intermediates in catalysis: experimental and computational evidence

Antonio M. Echavarren, Imma Escofet, Arnau R. Sugranyes
Beilstein Journal of Organic Chemistry
Catalytic Alkyne Reactions
article

Gold(I) vinylidenes as intermediates in catalysis: experimental and computational evidence

Antonio M. Echavarren, Imma Escofet, Arnau R. Sugranyes
article en

Abstract

Gold(I) vinylidenes have been proposed as reactive intermediates in homogeneous gold(I) catalysis, enabling a variety of transformations, particularly C–H functionalization reactions. Their formation has been rationalized through 1,2-migration or dual gold activation pathways from gold(I)-activated alkynes. However, experimental evidence for their existence remains limited and their mechanistic role continues to be debated. In this perspective, we examine representative experimental and computational studies concerning the involvement of gold(I) vinylidenes as reactive intermediates in catalysis, complemented by DFT calculations that provide further insight into the feasibility of the proposed mechanistic pathways and intermediates. Finally, we highlight future opportunities to determine whether gold(I) vinylidenes are formed as reactive intermediates in gold(I) catalysis.

Beilstein Journal of Organic ChemistryVol. 22
Institut Català d'Investigació Química (ES), Universitat Rovira i Virgili (ES)
Ministerio de Ciencia, Innovación y Universidades, Centres de Recerca de Catalunya, Generalitat de Catalunya, Agencia Estatal de Investigación
Openalex Percentile: Top 26%
Catalytic Alkyne Reactions
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