Palladium-catalyzed domino N-arylation/carbopalladation/C-H functionalization: three-component synthesis of 3-(diarylmethylene)oxindoles

A palladium-catalyzed 3-component synthesis of 3-(diarylmethylene)indolin-2-ones was developed. A sequence of intermol. N-arylation/intermol. carbopalladation/C-H activation/C-C bond formation was realized in a 1-pot fashion allowing the construction of 1 C-N bond and 2 C-C bonds by way of 3 distinct catalytic cycles. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 50, 26, 3602-3605
Year:
2009
Keywords:
Iodides Role: RCT (Reactant) ; RACT (Reactant or reagent) (aryl; prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide ; aryl iodide ; and alkynamide using palladium catalyst); Lactams Role: SPN (Synthetic preparation) ; PREP (Preparation) (bicyclic; prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide ; aryl iodide ; and alkynamide using palladium catalyst); Aryl halides Role: RCT (Reactant) ; RACT (Reactant or reagent) (iodides; prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide ; aryl iodide ; and alkynamide using palladium catalyst); Bicyclic compounds Role: SPN (Synthetic preparation) ; PREP (Preparation) (lactams; prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide ; aryl iodide ; and alkynamide using palladium catalyst); Metalation (palladation; prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide ; aryl iodide ; and alkynamide using palladium catalyst); Arylation; Cyclization catalysts; Heterocyclization catalysts; Multicomponent reaction (prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide ; aryl iodide ; and alkynamide using palladium catalyst); Aryl bromides Role: RCT (Reactant) ; RACT (Reactant or reagent) (prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide ; aryl iodide ; and alkynamide using palladium catalyst); Multicomponent reaction (three-component; prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide ; aryl iodide ; and alkynamide using palladium catalyst); Amides Role: RCT (Reactant) ; RACT (Reactant or reagent) (alpha ; beta -unsatd.; prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide ; aryl iodide ; and alkynamide using palladium catalyst) ; aryl halide alkynamide three component heterocyclization palladium catalyst; oxindole arylmethylene prepn; indolone arylmethylene prepn
Note:
CAN 151:148065
27-11
Heterocyclic Compounds (One Hetero Atom)
Institut de Chimie des Substances Naturelles, CNRS,Gif-sur-Yvette,Fr.
Journal
0040-4039
written in English.
3375-31-3 (Palladium diacetate); 161265-03-8 (Xantphos) Role: CAT (Catalyst use), USES (Uses) (prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide, aryl iodide, and alkynamide using palladium catalyst); 90-90-4 (4-Bromobenzophenone); 586-78-7 (4-Nitrophenyl bromide); 591-50-4 (Phenyl iodide); 609-73-4 (2-Nitrophenyl iodide); 619-42-1 (Methyl 4-bromobenzoate); 623-00-7 (4-Bromobenzonitrile); 696-62-8 (4-Methoxyphenyl iodide); 1122-91-4 (4-Bromobenzaldehyde); 26218-49-5; 55330-55-7; 197231-97-3 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide, aryl iodide, and alkynamide using palladium catalyst); 914785-65-2P; 1039396-03-6P; 1170306-78-1P; 1170306-79-2P; 1170306-80-5P; 1170306-81-6P; 1170306-82-7P; 1170306-83-8P; 1170306-84-9P; 1170306-85-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of (arylmethylene)oxindoles by three-component coupling of aryl bromide, aryl iodide, and alkynamide using palladium catalyst)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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