Room-Temperature ortho -Alkoxylation and -Halogenation of N -Tosylbenzamides by Using Palladium(II)-Catalyzed CH Activation - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2014

Room-Temperature ortho -Alkoxylation and -Halogenation of N -Tosylbenzamides by Using Palladium(II)-Catalyzed CH Activation

Résumé

The N‐tosylcarboxamide group can direct the room‐temperature palladium‐catalyzed CH alkoxylation and halogenation of substituted arenes in a simple and mild procedure. The room‐temperature stoichiometric cyclopalladation of N‐tosylbenzamide was first studied, and the ability of the palladacycle to react with oxidants to form CX and CO bonds under mild conditions was demonstrated. The reaction conditions were then adapted to promote room‐temperature ortho‐alkoxylations and ortho‐halogenations of N‐tosylbenzamides using palladium as catalyst. The scope and limitation of both alkoxylations and halogenations was studied and the subsequent functional transformation of the N‐tosylcarboxamide group through nucleophilic additions was evaluated. This methodology offers a simple and mild route to diversely functionalized arenes.

Domaines

Chimie organique

Dates et versions

hal-02011110 , version 1 (07-02-2019)

Identifiants

Citer

Florent Péron, Christine Fossey, Jana Sopkova-de Oliveira Santos, Thomas Cailly, Frédéric Fabis. Room-Temperature ortho -Alkoxylation and -Halogenation of N -Tosylbenzamides by Using Palladium(II)-Catalyzed CH Activation. Chemistry - A European Journal, 2014, 20 (24), pp.7507-7513. ⟨10.1002/chem.201303923⟩. ⟨hal-02011110⟩
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