research article

Palladium-catalyzed domino N-arylation/carbopalladation/C-H functionalization: three-component synthesis of 3-(diarylmethylene)oxindoles

Pinto, Artur
•
Neuville, Luc
•
Zhu, Jieping  
2009
Tetrahedron Letters

A palladium-catalyzed 3-component synthesis of 3-(diarylmethylene)indolin-2-ones was developed. A sequence of intermol. N-arylation/intermol. carbopalladation/C-H activation/C-C bond formation was realized in a 1-pot fashion allowing the construction of 1 C-N bond and 2 C-C bonds by way of 3 distinct catalytic cycles. [on SciFinder (R)]

Type
research article
DOI
10.1016/j.tetlet.2009.03.086
Author(s)
Pinto, Artur
Neuville, Luc
Zhu, Jieping  
Date Issued

2009

Publisher

Elsevier

Published in
Tetrahedron Letters
Volume

50

Issue

26

Start page

3602

End page

3605

Subjects

Iodides Role: RCT (Reactant)

•

RACT (Reactant or reagent) (aryl; prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide

•

aryl iodide

•

and alkynamide using palladium catalyst); Lactams Role: SPN (Synthetic preparation)

•

PREP (Preparation) (bicyclic; prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide

•

aryl iodide

•

and alkynamide using palladium catalyst); Aryl halides Role: RCT (Reactant)

•

RACT (Reactant or reagent) (iodides; prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide

•

aryl iodide

•

and alkynamide using palladium catalyst); Bicyclic compounds Role: SPN (Synthetic preparation)

•

PREP (Preparation) (lactams; prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide

•

aryl iodide

•

and alkynamide using palladium catalyst); Metalation (palladation; prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide

•

aryl iodide

•

and alkynamide using palladium catalyst); Arylation; Cyclization catalysts; Heterocyclization catalysts; Multicomponent reaction (prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide

•

aryl iodide

•

and alkynamide using palladium catalyst); Aryl bromides Role: RCT (Reactant)

•

RACT (Reactant or reagent) (prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide

•

aryl iodide

•

and alkynamide using palladium catalyst); Multicomponent reaction (three-component; prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide

•

aryl iodide

•

and alkynamide using palladium catalyst); Amides Role: RCT (Reactant)

•

RACT (Reactant or reagent) (alpha

•

beta -unsatd.; prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide

•

aryl iodide

•

and alkynamide using palladium catalyst)

•

aryl halide alkynamide three component heterocyclization palladium catalyst; oxindole arylmethylene prepn; indolone arylmethylene prepn

Note

CAN 151:148065

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 diacetate); 161265-03-8 (Xantphos) Role: CAT (Catalyst use), USES (Uses) (prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide, aryl iodide, and alkynamide using palladium catalyst); 90-90-4 (4-Bromobenzophenone); 586-78-7 (4-Nitrophenyl bromide); 591-50-4 (Phenyl iodide); 609-73-4 (2-Nitrophenyl iodide); 619-42-1 (Methyl 4-bromobenzoate); 623-00-7 (4-Bromobenzonitrile); 696-62-8 (4-Methoxyphenyl iodide); 1122-91-4 (4-Bromobenzaldehyde); 26218-49-5; 55330-55-7; 197231-97-3 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide, aryl iodide, and alkynamide using palladium catalyst); 914785-65-2P; 1039396-03-6P; 1170306-78-1P; 1170306-79-2P; 1170306-80-5P; 1170306-81-6P; 1170306-82-7P; 1170306-83-8P; 1170306-84-9P; 1170306-85-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide, aryl iodide, and alkynamide using palladium catalyst)

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/20.500.14299/58392