Palladium-Catalyzed Carbo-Heterofunctionalization of Alkenes for the Synthesis of Oxindoles and Spirooxindoles

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)]


Published in:
Organic Letters, 12, 20, 4498-4501
Year:
2010
Keywords:
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)
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 Record created 2010-11-25, last modified 2018-09-13


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