Palladium-catalyzed annulation of acyloximes with arynes (or alkynes): synthesis of phenanthridines and isoquinolines
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)]
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Gerfaud, T., Neuville, L., & Zhu, J. (2009). Palladium-catalyzed annulation of acyloximes with arynes (or alkynes): synthesis of phenanthridines and isoquinolines. Angewandte Chemie International Edition, 48(3), 572–577. https://doi.org/10.1002/anie.200804683
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2009
48
3
572
577
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)
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