Palladium-Catalyzed Intramolecular C-Arylation of Benzylic Carbon: Synthesis of 3-Benzoxazolylisoindolinones by a Sequence of Ugi-4CR/Postfunctionalization
2008
Abstract
Submitting Ugi-adduct to two consecutive metal-catalyzed intramol. reactions, namely copper-catalyzed O-arylation and palladium-catalyzed C-arylation of benzylic carbon developed in the course of this study, affords the benzoxazolylisoindolinones, e.g., I, in good to excellent yields. [on SciFinder (R)]
Details
Title
Palladium-Catalyzed Intramolecular C-Arylation of Benzylic Carbon: Synthesis of 3-Benzoxazolylisoindolinones by a Sequence of Ugi-4CR/Postfunctionalization
Author(s)
Salcedo, Angela ; Neuville, Luc ; Zhu, Jieping
Published in
Journal of Organic Chemistry
Volume
73
Issue
9
Pages
3600-3603
Date
2008
ISSN
0022-3263
Keywords
Amides Role: RCT (Reactant); SPN (Synthetic preparation); PREP (Preparation); RACT (Reactant or reagent) (bisamides; prepn. of (benzoxazolyl)isoindolinones via copper-catalyzed intramol. O-arylation of Ugi adducts followed by palladium-catalyzed intramol. C-arylation); Arylation; Arylation catalysts (intramol.; prepn. of (benzoxazolyl)isoindolinones via copper-catalyzed intramol. O-arylation of Ugi adducts followed by palladium-catalyzed intramol. C-arylation); Heterocyclization; Heterocyclization catalysts; Ugi reaction (prepn. of (benzoxazolyl)isoindolinones via copper-catalyzed intramol. O-arylation of Ugi adducts followed by palladium-catalyzed intramol. C-arylation); Aldehydes Role: RCT (Reactant); RACT (Reactant or reagent) (prepn. of (benzoxazolyl)isoindolinones via copper-catalyzed intramol. O-arylation of Ugi adducts followed by palladium-catalyzed intramol. C-arylation); Amines Role: RCT (Reactant); RACT (Reactant or reagent) (primary; prepn. of (benzoxazolyl)isoindolinones via copper-catalyzed intramol. O-arylation of Ugi adducts followed by palladium-catalyzed intramol. C-arylation); Ugi adduct copper intramol arylation; benzoxazolylmethyl iodobenzamide deriv prepn palladium intramol arylation; isoindolinone benzoxazolyl deriv prepn; intramol arylation catalyst palladium
Note
CAN 148:495834
28-6
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
3375-31-3; 7681-65-4 (Copper(I) iodide) Role: CAT (Catalyst use), USES (Uses) (prepn. of (benzoxazolyl)isoindolinones via copper-catalyzed intramol. O-arylation of Ugi adducts followed by palladium-catalyzed intramol. C-arylation); 75-31-0 (Isopropylamine); 78-84-2 (2-Methylpropanal); 88-67-5 (2-Iodobenzoic acid); 100-46-9 (Benzylamine); 100-52-7 (Benzaldehyde); 109-73-9 (Butylamine); 111-71-7 (Heptanal); 123-72-8 (Butanal); 2393-23-9 (4-Methoxybenzylamine); 183209-25-8 (1-Iodo-2-isocyanobenzene); 1021558-51-9; 1021558-63-3 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of (benzoxazolyl)isoindolinones via copper-catalyzed intramol. O-arylation of Ugi adducts followed by palladium-catalyzed intramol. C-arylation); 1021558-45-1P; 1021558-57-5P; 1021558-69-9P; 1021558-75-7P; 1021558-81-5P; 1021558-87-1P; 1021558-92-8P; 1021558-98-4P; 1021559-09-0P; 1021559-16-9P; 1021559-21-6P; 1021559-32-9P; 1021559-38-5P; 1021559-44-3P; 1021559-92-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of (benzoxazolyl)isoindolinones via copper-catalyzed intramol. O-arylation of Ugi adducts followed by palladium-catalyzed intramol. C-arylation); 1021559-03-4P; 1021559-26-1P; 1021559-50-1P; 1021559-56-7P; 1021559-62-5P; 1021559-68-1P; 1021559-74-9P; 1021559-80-7P; 1021559-86-3P; 1021559-98-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of (benzoxazolyl)isoindolinones via copper-catalyzed intramol. O-arylation of Ugi adducts followed by palladium-catalyzed intramol. C-arylation)
28-6
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
3375-31-3; 7681-65-4 (Copper(I) iodide) Role: CAT (Catalyst use), USES (Uses) (prepn. of (benzoxazolyl)isoindolinones via copper-catalyzed intramol. O-arylation of Ugi adducts followed by palladium-catalyzed intramol. C-arylation); 75-31-0 (Isopropylamine); 78-84-2 (2-Methylpropanal); 88-67-5 (2-Iodobenzoic acid); 100-46-9 (Benzylamine); 100-52-7 (Benzaldehyde); 109-73-9 (Butylamine); 111-71-7 (Heptanal); 123-72-8 (Butanal); 2393-23-9 (4-Methoxybenzylamine); 183209-25-8 (1-Iodo-2-isocyanobenzene); 1021558-51-9; 1021558-63-3 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of (benzoxazolyl)isoindolinones via copper-catalyzed intramol. O-arylation of Ugi adducts followed by palladium-catalyzed intramol. C-arylation); 1021558-45-1P; 1021558-57-5P; 1021558-69-9P; 1021558-75-7P; 1021558-81-5P; 1021558-87-1P; 1021558-92-8P; 1021558-98-4P; 1021559-09-0P; 1021559-16-9P; 1021559-21-6P; 1021559-32-9P; 1021559-38-5P; 1021559-44-3P; 1021559-92-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of (benzoxazolyl)isoindolinones via copper-catalyzed intramol. O-arylation of Ugi adducts followed by palladium-catalyzed intramol. C-arylation); 1021559-03-4P; 1021559-26-1P; 1021559-50-1P; 1021559-56-7P; 1021559-62-5P; 1021559-68-1P; 1021559-74-9P; 1021559-80-7P; 1021559-86-3P; 1021559-98-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of (benzoxazolyl)isoindolinones via copper-catalyzed intramol. O-arylation of Ugi adducts followed by palladium-catalyzed intramol. C-arylation)
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Record creation date
2010-11-25