research article

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

Pinto, Artur
•
Neuville, Luc
•
Zhu, Jieping  
2007
Angewandte Chemie International Edition

[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)]

Type
research article
DOI
10.1002/anie.200605192
Author(s)
Pinto, Artur
Neuville, Luc
Zhu, Jieping  
Date Issued

2007

Publisher

Wiley-VCH Verlag GmbH

Published in
Angewandte Chemie International Edition
Volume

46

Issue

18

Start page

3291

End page

3295

Subjects

Iodides Role: RCT (Reactant)

•

RACT (Reactant or reagent) (aryl; prepn. of (diarylmethylene)oxindoles via palladium-copper-catalyzed three-component Sonogashira cross-coupling/cyclization of propiolamides with aryl iodides or heteroaryl iodides); Aryl halides Role: RCT (Reactant)

•

RACT (Reactant or reagent) (iodides; prepn. of (diarylmethylene)oxindoles via palladium-copper-catalyzed three-component Sonogashira cross-coupling/cyclization of propiolamides with aryl iodides or heteroaryl iodides); Cyclization; Sonogashira coupling reaction (prepn. of (diarylmethylene)oxindoles via palladium-copper-catalyzed three-component Sonogashira cross-coupling/cyclization of propiolamides with aryl iodides or heteroaryl iodides); Multicomponent reaction (three-component; prepn. of (diarylmethylene)oxindoles via palladium-copper-catalyzed three-component Sonogashira cross-coupling/cyclization of propiolamides with aryl iodides or heteroaryl iodides)

•

diarylmethyleneoxindole prepn; propiolamide iodoarene Sonogashira cross coupling cyclization palladium copper; palladium copper three component Sonogashira cross coupling cyclization catalyst

Note

CAN 147:143210

27-11

Heterocyclic Compounds (One Hetero Atom)

Institut de Chimie des Substances Naturelles, CNRS,Gif-sur-Yvette,Fr.

Journal

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)

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LSPN  
Available on Infoscience
November 25, 2010
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/58431