C(sp)-C(sp2) Bond Formation from Triflates via a Copper-Free Sonogashira Cross-Coupling

Abstract A rapid and copper-free Sonogashira cross-coupling enabling the direct use of aryl triflates as electrophiles is reported. The palladium-catalyzed protocol operates under simple and robust conditions, overcoming common limitations associated with triflate substrates. Broad scope is demonstrated across electron-rich, electron-neutral, moderately electron-deficient, and heteroaryl triflates, as well as diverse aromatic and aliphatic terminal alkynes. Extension to vinyl triflates further highlights the versatility of the method, offering a practical alternative to the use of corresponding aryl and vinyl halides for C(sp)-C(sp2) bond formation.

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Publication Details

Journal
ACS Omega
Published
2026-11-10
DOI
https://doi.org/10.1021/acsomega.6c07460
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
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article

C(sp)-C(sp2) Bond Formation from Triflates via a Copper-Free Sonogashira Cross-Coupling

Thomas Lemaître, Thomas Cailly, Charline Kieffer, Anne Sophie Voisin‐Chiret et al.
ACS Omega
Catalytic Cross-Coupling Reactions
article

C(sp)-C(sp2) Bond Formation from Triflates via a Copper-Free Sonogashira Cross-Coupling

Thomas Lemaître, Thomas Cailly, Charline Kieffer, Anne Sophie Voisin‐Chiret, Marie Cornu
article en

Abstract

Abstract A rapid and copper-free Sonogashira cross-coupling enabling the direct use of aryl triflates as electrophiles is reported. The palladium-catalyzed protocol operates under simple and robust conditions, overcoming common limitations associated with triflate substrates. Broad scope is demonstrated across electron-rich, electron-neutral, moderately electron-deficient, and heteroaryl triflates, as well as diverse aromatic and aliphatic terminal alkynes. Extension to vinyl triflates further highlights the versatility of the method, offering a practical alternative to the use of corresponding aryl and vinyl halides for C(sp)-C(sp2) bond formation.

ACS Omega
Inserm (FR), Normandie Université (FR), Centre Hospitalier Universitaire de Caen Normandie (FR), Cyceron (FR), Centre d'Etudes et de Recherche sur le Médicament de Normandie (FR), Université de Caen Normandie (FR)
Catalytic Cross-Coupling Reactions
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