Palladium-catalyzed annulation of acyloximes with arynes (or alkynes): synthesis of phenanthridines and isoquinolines
2009
Résumé
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)]
Détails
Titre
Palladium-catalyzed annulation of acyloximes with arynes (or alkynes): synthesis of phenanthridines and isoquinolines
Auteur(s)
Gerfaud, Thibaud ; Neuville, Luc ; Zhu, Jieping
Publié dans
Angewandte Chemie, International Edition
Volume
48
Numéro
3
Pages
572-577
Date
2009
ISSN
1433-7851
Mots-clés (libres)
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)
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)
Laboratoires
LSPN
Le document apparaît dans
Production scientifique et compétences > SB - Faculté des sciences de base > ISIC - Institut des sciences et ingénierie chimiques > LSPN - Laboratoire de synthèse et produits naturels
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Date de création de la notice
2010-11-25