Synthesis of 3-(Diarylmethylenyl)oxindole by a Palladium-Catalyzed Domino Carbopalladation/C-H Activation/C-C Bond-Forming Process
2006
Abstract
A highly efficient palladium-catalyzed synthesis of unsym. substituted 3-(diarylmethylenyl)indolinones from readily accessible starting materials is developed. The domino reaction involves a sequence of intermol. carbopalladation, C-H activation, and C-C bond formation. A plausible mechanistic pathway for the reaction is discussed on the basis of the kinetic isotope effect [KH/KD (intermol.) = 1, KH/KD (intramol.) = 2.7] as well as the electronic effect. [on SciFinder (R)]
Details
Title
Synthesis of 3-(Diarylmethylenyl)oxindole by a Palladium-Catalyzed Domino Carbopalladation/C-H Activation/C-C Bond-Forming Process
Author(s)
Pinto, Artur ; Neuville, Luc ; Retailleau, Pascal ; Zhu, Jieping
Published in
Organic Letters
Volume
8
Issue
21
Pages
4927-4930
Date
2006
ISSN
1523-7060
Note
CAN 145:489084
27-11
Heterocyclic Compounds (One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
3375-31-3 (Palladium(II) acetate) Role: CAT (Catalyst use), USES (Uses) (prepn. of 3-(diarylmethylenyl)oxindole by a palladium-catalyzed domino carbopalladation/C-H activation/C-C bond-forming process); 914785-51-6P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (prepn. of 3-(diarylmethylenyl)oxindole by a palladium-catalyzed domino carbopalladation/C-H activation/C-C bond-forming process); 529-28-2 (2-Iodoanisole); 591-50-4 (Iodobenzene); 609-73-4 (1-Iodo-2-nitrobenzene); 615-37-2 (2-Iodotoluene); 637-44-5 (Phenylpropiolic acid); 637-87-6; 766-85-8 (3-Iodoanisole); 3422-01-3 (N-tert.-Butoxycarbonylaniline); 14545-23-4 (Heptadeuteroaniline); 90585-26-5 (N-(2-Iodophenyl)-N-methylacetamide); 94298-51-8; 111054-32-1; 914785-45-8; 914785-46-9; 914785-47-0; 914785-48-1; 914785-49-2; 914785-50-5; 914785-71-0 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of 3-(diarylmethylenyl)oxindole by a palladium-catalyzed domino carbopalladation/C-H activation/C-C bond-forming process); 914785-66-3P; 914785-67-4P; 914785-68-5P; 914785-69-6P; 918958-93-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of 3-(diarylmethylenyl)oxindole by a palladium-catalyzed domino carbopalladation/C-H activation/C-C bond-forming process); 914785-52-7P; 914785-53-8P; 914785-54-9P; 914785-55-0P; 914785-56-1P; 914785-57-2P; 914785-58-3P; 914785-59-4P; 914785-60-7P; 914785-61-8P; 914785-62-9P; 914785-63-0P; 914785-64-1P; 914785-65-2P; 914785-72-1P; 914785-73-2P; 914785-74-3P; 914785-75-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of 3-(diarylmethylenyl)oxindole by a palladium-catalyzed domino carbopalladation/C-H activation/C-C bond-forming process)
27-11
Heterocyclic Compounds (One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
3375-31-3 (Palladium(II) acetate) Role: CAT (Catalyst use), USES (Uses) (prepn. of 3-(diarylmethylenyl)oxindole by a palladium-catalyzed domino carbopalladation/C-H activation/C-C bond-forming process); 914785-51-6P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (prepn. of 3-(diarylmethylenyl)oxindole by a palladium-catalyzed domino carbopalladation/C-H activation/C-C bond-forming process); 529-28-2 (2-Iodoanisole); 591-50-4 (Iodobenzene); 609-73-4 (1-Iodo-2-nitrobenzene); 615-37-2 (2-Iodotoluene); 637-44-5 (Phenylpropiolic acid); 637-87-6; 766-85-8 (3-Iodoanisole); 3422-01-3 (N-tert.-Butoxycarbonylaniline); 14545-23-4 (Heptadeuteroaniline); 90585-26-5 (N-(2-Iodophenyl)-N-methylacetamide); 94298-51-8; 111054-32-1; 914785-45-8; 914785-46-9; 914785-47-0; 914785-48-1; 914785-49-2; 914785-50-5; 914785-71-0 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of 3-(diarylmethylenyl)oxindole by a palladium-catalyzed domino carbopalladation/C-H activation/C-C bond-forming process); 914785-66-3P; 914785-67-4P; 914785-68-5P; 914785-69-6P; 918958-93-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of 3-(diarylmethylenyl)oxindole by a palladium-catalyzed domino carbopalladation/C-H activation/C-C bond-forming process); 914785-52-7P; 914785-53-8P; 914785-54-9P; 914785-55-0P; 914785-56-1P; 914785-57-2P; 914785-58-3P; 914785-59-4P; 914785-60-7P; 914785-61-8P; 914785-62-9P; 914785-63-0P; 914785-64-1P; 914785-65-2P; 914785-72-1P; 914785-73-2P; 914785-74-3P; 914785-75-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of 3-(diarylmethylenyl)oxindole by a palladium-catalyzed domino carbopalladation/C-H activation/C-C bond-forming process)
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LSPN
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Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
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Peer-reviewed publications
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Published
Record creation date
2010-11-25