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

• Published in: Angewandte Chemie, International Edition, vol. 48, num. 3, p. 572-577
• Publication date: 2009

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)]

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)

Reference

• EPFL-ARTICLE-158050
• doi:10.1002/anie.200804683

Record created on 2010-11-25, modified on 2017-05-12