Palladium-catalyzed three-component synthesis of 3-(diarylmethylene)oxindoles through a domino Sonogashira/carbopalladation/C-H activation/C-C bond-forming sequence

[Pd(PPh3)4]/Cul served as an efficient catalyst for the reaction of three readily available starting materials to give 3-(diarylmethylene)indolin-2-ones, e.g., I, through a sequence of intermol. Sonogashira reaction/intermol. carbopalladation/C-H activation/C-C bond formation. Three C-C bonds were thereby formed as a result of three distinct catalytic cycles with one catalyst. [on SciFinder (R)]


Published in:
Angewandte Chemie, International Edition, 46, 18, 3291-3295
Year:
2007
Keywords:
Note:
CAN 147:143210
27-11
Heterocyclic Compounds (One Hetero Atom)
Institut de Chimie des Substances Naturelles, CNRS,Gif-sur-Yvette,Fr.
Journal
1433-7851
written in English.
7681-65-4 (Copper(I) iodide); 14221-01-3 (Tetrakis(triphenylphosphine)palladium) Role: CAT (Catalyst use), USES (Uses) (prepn. of (diarylmethylene)oxindoles via palladium-copper-catalyzed three-component Sonogashira cross-coupling/cyclization of propiolamides with aryl iodides or heteroaryl iodides); 401-81-0 (1-Iodo-3-trifluoromethylbenzene); 591-50-4 (Iodobenzene); 609-73-4 (1-Iodo-2-nitrobenzene); 636-98-6 (4-Nitroiodobenzene); 637-87-6 (1-Chloro-4-iodobenzene); 696-62-8 (4-Methoxyiodobenzene); 1120-90-7 (3-Iodopyridine); 3437-95-4 (2-Iodothiophene); 5029-67-4 (2-Iodopyridine); 16066-91-4 (5-Iodoindole); 86576-73-0; 943452-32-2; 943452-33-3; 1010395-59-1 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of (diarylmethylene)oxindoles via palladium-copper-catalyzed three-component Sonogashira cross-coupling/cyclization of propiolamides with aryl iodides or heteroaryl iodides); 914785-51-6P; 914785-54-9P; 943452-34-4P; 943452-35-5P; 943452-36-6P; 943452-37-7P; 943452-38-8P; 943452-39-9P; 943452-40-2P; 943452-41-3P; 943452-42-4P; 943452-43-5P; 943452-44-6P; 943452-45-7P; 943452-46-8P; 943452-47-9P; 943452-48-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of (diarylmethylene)oxindoles via palladium-copper-catalyzed three-component Sonogashira cross-coupling/cyclization of propiolamides with aryl iodides or heteroaryl iodides); 914785-45-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of N-methyl-N-(methoxyphenyl) phenylpropiolamide via Sonogashira cross-coupling of N-methyl-N-(methoxyphenyl) propiolamide with iodobenzene)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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