On the Mechanism of the Digold(I)–Hydroxide‐Catalysed Hydrophenoxylation of Alkynes - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2015

On the Mechanism of the Digold(I)–Hydroxide‐Catalysed Hydrophenoxylation of Alkynes

Adrián Gómez-Suárez
  • Fonction : Auteur
Yoshihiro Oonishi
  • Fonction : Auteur
Sai Vummaleti
  • Fonction : Auteur
David Nelson
  • Fonction : Auteur
David Cordes
  • Fonction : Auteur
Alexandra Slawin
  • Fonction : Auteur
Luigi Cavallo
  • Fonction : Auteur
Steven Nolan
  • Fonction : Auteur
Albert Poater
  • Fonction : Auteur

Résumé

Abstract Herein, we present a detailed investigation of the mechanistic aspects of the dual gold‐catalysed hydrophenoxylation of alkynes by both experimental and computational methods. The dissociation of [{Au(NHC)} 2 (μ‐OH)][BF 4 ] is essential to enter the catalytic cycle, and this step is favoured by the presence of bulky, non‐coordinating counter ions. Moreover, in silico studies confirmed that phenol does not only act as a reactant, but also as a co‐catalyst, lowering the energy barriers of several transition states. A gem ‐diaurated species might form during the reaction, but this lies deep within a potential energy well, and is likely to be an “off‐cycle” rather than an “in‐cycle” intermediate.

Domaines

Catalyse

Dates et versions

hal-04599370 , version 1 (03-06-2024)

Identifiants

Citer

Adrián Gómez-Suárez, Yoshihiro Oonishi, Anthony Martin, Sai Vummaleti, David Nelson, et al.. On the Mechanism of the Digold(I)–Hydroxide‐Catalysed Hydrophenoxylation of Alkynes. Chemistry - A European Journal, 2015, 22 (3), pp.1125-1132. ⟨10.1002/chem.201503097⟩. ⟨hal-04599370⟩
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