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  4. Palladium-catalyzed annulation of acyloximes with arynes (or alkynes): synthesis of phenanthridines and isoquinolines
 
research article

Palladium-catalyzed annulation of acyloximes with arynes (or alkynes): synthesis of phenanthridines and isoquinolines

Gerfaud, Thibaud
•
Neuville, Luc
•
Zhu, Jieping  
2009
Angewandte Chemie International Edition

A palladium-catalyzed domino aminopalladation/C-H functionalization sequence has been developed, and provides access to functionalized phenanthridines and isoquinolines. The use of butyronitrile as the solvent is determinant to the success of the domino process. [on SciFinder (R)]

  • Details
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Type
research article
DOI
10.1002/anie.200804683
Author(s)
Gerfaud, Thibaud
Neuville, Luc
Zhu, Jieping  
Date Issued

2009

Publisher

Wiley-VCH Verlag GmbH

Published in
Angewandte Chemie International Edition
Volume

48

Issue

3

Start page

572

End page

577

Subjects

Ketones Role: RCT (Reactant)

•

RACT (Reactant or reagent) (aryl; prepn. of pentafluorobenzoyl oximes via condensation of ketones with hydroxyamine followed by esterification with pentafluorobenzoyl chloride

•

and their use in prepn. of phenanthridines and isoquinolines); Alkynes; Aromatic hydrocarbons Role: RCT (Reactant)

•

SPN (Synthetic preparation)

•

PREP (Preparation)

•

RACT (Reactant or reagent) (arynes; prepn. of phenanthridines and isoquinolines via palladium-catalyzed annulation of acyloximes with in situ generated benzyne from silylphenyl triflates); Cyclization (prepn. of phenanthridines and isoquinolines via palladium-catalyzed annulation of acyloximes with in situ generated benzyne from silylphenyl triflates)

•

phenanthridine prepn; isoquinoline prepn; acyloxime prepn aryne annulation palladium

Note

CAN 150:329592

27-17

Heterocyclic Compounds (One Hetero Atom)

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

Journal

written in English.

90-98-2; 98-86-2 (Acetophenone); 100-19-6; 119-61-9 (Benzophenone); 345-92-6; 611-70-1 (Isopropyl phenyl ketone); 611-97-2; 704-38-1; 1151-94-6; 1868-00-4; 2251-50-5 (Pentafluorobenzoyl chloride); 21221-91-0; 21382-50-3; 32446-66-5 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of pentafluorobenzoyl oximes via condensation of ketones with hydroxyamine followed by esterification with pentafluorobenzoyl chloride, and their use in prepn. of phenanthridines and isoquinolines); 12012-95-2 (Diallyldichlorodipalladium) Role: CAT (Catalyst use), USES (Uses) (prepn. of phenanthridines and isoquinolines via palladium-catalyzed annulation of acyloximes with in situ generated benzyne from silylphenyl triflates); 71-43-2 (Benzene); 762-42-5; 88284-48-4; 217813-03-1; 458566-99-9; 780820-43-1; 881009-83-2 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of phenanthridines and isoquinolines via palladium-catalyzed annulation of acyloximes with in situ generated benzyne from silylphenyl triflates); 479675-59-7P; 1026685-05-1P; 1131328-85-2P; 1131328-87-4P; 1131328-89-6P; 1131328-91-0P; 1131328-93-2P; 1131328-95-4P; 1131328-97-6P; 1131328-99-8P; 1131329-01-5P; 1131329-35-5P; 1131329-39-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of phenanthridines and isoquinolines via palladium-catalyzed annulation of acyloximes with in situ generated benzyne from silylphenyl triflates); 2720-93-6P; 3955-65-5P; 16573-52-7P; 31150-40-0P; 182057-99-4P; 182058-06-6P; 182058-19-1P; 862587-29-9P; 864061-09-6P; 1131329-10-6P; 1131329-13-9P; 1131329-16-2P; 1131329-18-4P; 1131329-20-8P; 1131329-22-0P; 1131329-24-2P; 1131329-26-4P; 1131329-28-6P; 1131329-30-0P; 1131329-32-2P; 1131329-46-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of phenanthridines and isoquinolines via palladium-catalyzed annulation of acyloximes with in situ generated benzyne from silylphenyl triflates)

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/20.500.14299/58395
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