Palladium-Catalyzed Carbo-Heterofunctionalization of Alkenes for the Synthesis of Oxindoles and Spirooxindoles
2010
Résumé
A palladium-catalyzed oxidative carbo-heterofunctionalization of aniline derivs. involving concomitant direct C-H functionalization and C-X bond formation was developed. By simply changing the reaction conditions (solvent and catalyst), either 3,3'-disubstituted oxindole or spirooxindole was accessible from the same starting material. E.g., reaction of acrylanilide I in presence of Pd(OAc)2 and PhI(OAc)2 gave 54% oxindole II. [on SciFinder (R)]
Détails
Titre
Palladium-Catalyzed Carbo-Heterofunctionalization of Alkenes for the Synthesis of Oxindoles and Spirooxindoles
Auteur(s)
Jaegli, Stephanie ; Dufour, Jeremy ; Wei, Hai-long ; Piou, Tiffany ; Duan, Xin-Hua ; Vors, Jean-Pierre ; Neuville, Luc ; Zhu, Jieping
Publié dans
Organic Letters
Volume
12
Numéro
20
Pages
4498-4501
Date
2010
Mots-clés (libres)
Acetoxylation; Acetoxylation catalysts; Cyclization; Cyclization catalysts; Spirocyclization; Spirocyclization catalysts (palladium-catalyzed oxidative carbo-heterofunctionalization of acrylanilides for the synthesis of oxindoles and spirooxindoles); Anilides Role: RCT (Reactant); RACT (Reactant or reagent) (palladium-catalyzed oxidative carbo-heterofunctionalization of acrylanilides for the synthesis of oxindoles and spirooxindoles); palladium catalyst oxidative cyclization spirocyclization acetoxylation acrylanilide; oxindole spirooxindole prepn
Note
CAN 153:505623, 27-20, Heterocyclic Compounds (One Hetero Atom), Institut de Chimie des Substances Naturelles,Centre de Recherche de Gif, CNRS,Gif-sur-Yvette,Fr., Journal, 1523-7060, written in English., 3375-31-3; 7647-10-1 (Palladium chloride (PdCl2) Role: CAT (Catalyst use), USES (Uses) (palladium-catalyzed oxidative carbo-heterofunctionalization of acrylanilides for the synthesis of oxindoles and spirooxindoles); 10579-60-9; 15796-89-1; 74480-63-0; 85576-99-4; 200128-36-5; 294642-84-5; 860426-07-9; 1247767-81-2; 1247767-86-7; 1247767-87-8; 1247767-91-4; 1247767-93-6; 1247767-99-2; 1247768-01-9; 1247768-03-1; 1247768-05-3; 1247768-51-9 Role: RCT (Reactant), RACT (Reactant or reagent) (palladium-catalyzed oxidative carbo-heterofunctionalization of acrylanilides for the synthesis of oxindoles and spirooxindoles); 3240-34-4 ((Diacetoxyiodo)benzene) Role: RGT (Reagent), RACT (Reactant or reagent) (palladium-catalyzed oxidative carbo-heterofunctionalization of acrylanilides for the synthesis of oxindoles and spirooxindoles); 1234787-48-4P; 1234787-62-2P; 1247768-09-7P; 1247768-11-1P; 1247768-12-2P; 1247768-16-6P; 1247768-18-8P; 1247768-20-2P; 1247768-23-5P; 1247768-24-6P; 1247768-28-0P; 1247768-34-8P; 1247768-35-9P; 1247768-40-6P; 1247768-41-7P; 1247768-42-8P; 1247768-46-2P; 1247768-48-4P; 1247768-49-5P; 1247768-50-8P; 1247768-55-3P Role: SPN (Synthetic preparation), PREP (Preparation) (palladium-catalyzed oxidative carbo-heterofunctionalization of acrylanilides for the synthesis of oxindoles and spirooxindoles)
Laboratoires
LSPN
Le document apparaît dans
Production scientifique et compétences > SB - Faculté des sciences de base > ISIC - Institut des sciences et ingénierie chimiques > LSPN - Laboratoire de synthèse et produits naturels
Publications validées par des pairs
Travail hors EPFL
Articles de journaux
Publié
Publications validées par des pairs
Travail hors EPFL
Articles de journaux
Publié
Date de création de la notice
2010-11-25