Investigation of the K 4 [Fe(CN) 6 ] mediated mono-and bispalladium-catalyzed cyanation of the benzothioxanthene core - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2021

Investigation of the K 4 [Fe(CN) 6 ] mediated mono-and bispalladium-catalyzed cyanation of the benzothioxanthene core

Pablo Simón Marqués
Laura Abad Galan
  • Fonction : Auteur
Magali Allain
Olivier Maury
Tangui Le Bahers
Philippe Blanchard
Clément Cabanetos

Résumé

The pallado-catalyzed cyanation of benzothioxanthene imide (BTXI) derivatives is explored herein. Once optimized on the monobromo BTXI, mild reaction conditions were successfully applied to the dibromo derivative affording two regioisomers that have been isolated and structurally solved. Additional hydrogen-deuterium exchange experiments were carried out to support a proposed mechanism involving the formation of a five-membered palladacycle intermediate in the bay area. In addition to impact the structural, photo physical and electrochemical properties of the BTXI core, nitrile moieties were successfully used as orthogonal protecting groups thus opening doors to new design principles.

Domaines

Chimie
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Dates et versions

hal-03389384 , version 1 (21-10-2021)

Identifiants

Citer

Pablo Simón Marqués, José María Andrés Castán, Laura Abad Galan, Magali Allain, Olivier Maury, et al.. Investigation of the K 4 [Fe(CN) 6 ] mediated mono-and bispalladium-catalyzed cyanation of the benzothioxanthene core. Journal of Organic Chemistry, 2021, 86 (8), pp.5901-5907. ⟨10.1021/acs.joc.1c00318⟩. ⟨hal-03389384⟩
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