Cyclic Diaryl λ 3 -Chloranes: Reagents and Their C–C and C–O Couplings with Phenols via Aryne Intermediates - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of the American Chemical Society Année : 2022

Cyclic Diaryl λ 3 -Chloranes: Reagents and Their C–C and C–O Couplings with Phenols via Aryne Intermediates

Torben Rogge
K N Houk
Joanna Wencel-Delord

Résumé

Hypervalent chloranes are a class of rare and poorly explored reagents. Their unique electronic properties confer them reactivity that is complementary to that of the common iodanes and emerging bromanes. Highly chemo-and regio-selective, metalfree and mild CC and CO couplings are reported here. Experimental and computational mechanistic studies elucidate the unprecedented reactivities and selectivities of these systems and the intermediacy of aryne intermediates. The synthetic potential of these transformations is further demonstrated via post-functionalization of CC and CO coupling products obtained from reactions of chloranes with phenols under different conditions.
Fichier principal
Vignette du fichier
Cl-phenol coupling.pdf (1.89 Mo) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)

Dates et versions

hal-04415921 , version 1 (24-01-2024)

Identifiants

Citer

Matteo Lanzi, Torben Rogge, Tan Sang Truong, K N Houk, Joanna Wencel-Delord. Cyclic Diaryl λ 3 -Chloranes: Reagents and Their C–C and C–O Couplings with Phenols via Aryne Intermediates. Journal of the American Chemical Society, 2022, 145 (1), pp.345-358. ⟨10.1021/jacs.2c10090⟩. ⟨hal-04415921⟩
2 Consultations
6 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More