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

Gerfaud, Thibaud; Neuville, Luc; Zhu, Jieping

doi:10.1002/anie.200804683

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

Gerfaud, Thibaud ; Neuville, Luc ; Zhu, Jieping

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)]

Published in:

Angewandte Chemie, International Edition, 48, 3, 572-577

Year:

2009

Keywords:

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
1433-7851
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)

DOI:

10.1002/anie.200804683

Laboratories:

LSPN

Record appears in:

Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published