Palladium-Catalyzed Three-Component Synthesis of 3-(Diarylmethylene)oxindoles through a Domino Sonagashira/Carbopalladation/CH Activation/CC Bond-Forming Sequence

3‐3‐1 Formation: [Pd(PPh3)4]/CuI serves as an efficient catalyst for the reaction of three readily available starting materials to give 3‐(diarylmethylene)indolin‐2‐ones 3 through a sequence of intermolecular Sonagashira reaction/intermolecular carbopalladation/CH activation/CC bond formation (see...

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Published inAngewandte Chemie (International ed.) Vol. 46; no. 18; pp. 3291 - 3295
Main Authors Pinto, Artur, Neuville, Luc, Zhu, Jieping
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.01.2007
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
CH activation
domino reactions
multicomponent reactions
nitrogen heterocycles
palladium
Physical Sciences
Science & Technology
multicomponent reactions
ORGANIC-SYNTHESIS
DIRECT ARYLATION
HECK
ISOMERIZATION
TERMINAL ALKYNES
FUNCTIONALIZATION
C-H activation
domino reactions
3-ALKYLIDENEOXINDOLES
nitrogen heterocycles
COUPLING REACTION
palladium
STEREOSELECTIVE-SYNTHESIS
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Summary:3‐3‐1 Formation: [Pd(PPh3)4]/CuI serves as an efficient catalyst for the reaction of three readily available starting materials to give 3‐(diarylmethylene)indolin‐2‐ones 3 through a sequence of intermolecular Sonagashira reaction/intermolecular carbopalladation/CH activation/CC bond formation (see scheme). Three CC bonds are thereby formed as a result of three distinct catalytic cycles with one catalyst. DMF=N,N‐dimethylformamide.
Bibliography:ark:/67375/WNG-96QHRT4C-S
CNRS
ArticleID:ANIE200605192
istex:54EFDA3FE1DFB1C5C3D6E3B29660750DC3CA8BD5
Financial support from the CNRS and the Institut de Chimie des Substances Naturelles, CNRS, is gratefully acknowledged. A.P. thanks the "Ministère de l'Enseignement Supérieur et de la Recherche" for a doctoral fellowship.
Financial support from the CNRS and the Institut de Chimie des Substances Naturelles, CNRS, is gratefully acknowledged. A.P. thanks the “Ministère de l'Enseignement Supérieur et de la Recherche” for a doctoral fellowship.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200605192