Abstract
The palladium-catalyzed intramolecular N-arylation of the Blaise reaction intermediate, formed by reaction of nitriles with an in situ generated Reformatsky reagent from ethyl -bromo - (2-bromophenyl)acetate and zinc, afforded indoles in good yields. Extension of this approach to the chemoselective intramolecular N-alkylation/palladium-catalyzed N-arylation of the Blaise reaction intermediate, having -chloroalkyl appendages, provided a novel route for the tandem one-pot synthesis of N-fused indole derivatives. In contrast, the intermolecular coupling reaction of the Blaise reaction intermediates with 1,2-dihalobenzene did not proceed in the presence of a palladium catalyst, but proceeded in the presence of copper(I) iodide as the catalyst and resulted in indoles. 1 Introduction 2 Results and Discussion 2.1 Palladium-Catalyzed Intramolecular C-N Coupling Reaction of the Blaise Reaction Intermediate 2.2 Chemoselective Intramolecular N-Alkylation/Palladium-Catalyzed C-N Coupling Reaction of the Blaise Reaction Intermediate 2.3 Copper-Catalyzed Intermolecular N-C/C-C Coupling Reaction of the Blaise Reaction Intermediate with 1,2-Dihaloarenes 3 Conclusion.
Original language | English |
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Pages (from-to) | 1464-1476 |
Number of pages | 13 |
Journal | Synthesis (Germany) |
Volume | 44 |
Issue number | 10 |
DOIs | |
State | Published - 2012 |
Keywords
- Blaise reaction
- copper
- coupling
- indoles
- palladium
- tandem reaction