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Literature DB >> 23013049

Palladium-catalyzed annulation of arynes by o-halobenzamides: synthesis of phenanthridinones.

Chun Lu¹, Anton V Dubrovskiy, Richard C Larock.

Abstract

The palladium-catalyzed annulation of arynes by substituted o-halobenzamides produces N-substituted phenanthridinones in good yields. This methodology provides this important heterocyclic ring system in a single step by simultaneous C-C and C-N bond formation, under relatively mild reaction conditions, and tolerates a variety of functional groups.

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Year: 2012 PMID： 23013049 PMCID： PMC3490708 DOI： 10.1021/jo3016192

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

42 in total

1. Transition Metal-Catalyzed Carbocyclizations in Organic Synthesis.

Authors: Iwao Ojima; Maria Tzamarioudaki; Zhaoyang Li; Robert J. Donovan
Journal: Chem Rev Date: 1996-03-28 Impact factor: 60.622

2. Arynes in transition-metal-free multicomponent coupling reactions.

Authors: Sachin Suresh Bhojgude; Akkattu T Biju
Journal: Angew Chem Int Ed Engl Date: 2012-01-13 Impact factor: 15.336

3. Solvent/base effects in the selective domino synthesis of phenanthridinones that involves high-valent palladium species: experimental and theoretical studies.

Authors: Ludovic Donati; Pascale Leproux; Elise Prost; Sylvie Michel; François Tillequin; Vincent Gandon; François-Hugues Porée
Journal: Chemistry Date: 2011-09-27 Impact factor: 5.236

Palladium-catalyzed annulation of arynes by o-halobenzamides: synthesis of phenanthridinones.

1. Transition Metal-Catalyzed Carbocyclizations in Organic Synthesis.

2. Arynes in transition-metal-free multicomponent coupling reactions.

3. Solvent/base effects in the selective domino synthesis of phenanthridinones that involves high-valent palladium species: experimental and theoretical studies.

4. Synthesis of fused polycyclic aromatics by palladium-catalyzed annulation of arynes using 2-halobiaryls.

5. Synthesis of substituted 5[H]phenanthridin-6-ones as potent poly(ADP-ribose)polymerase-1 (PARP1) inhibitors.

6. One-pot synthesis of 1-alkyl-1H-indazoles from 1,1-dialkylhydrazones via aryne annulation.

7. Synthesis of pyrido[1,2-a]indole malonates and amines through aryne annulation.

8. Selective unusual Pd-mediated biaryl coupling reactions: solvent effects with carbonate bases.

9. An efficient process for pd-catalyzed C-N cross-coupling reactions of aryl iodides: insight into controlling factors.

10. Copper-catalyzed three-component coupling of arynes, terminal alkynes and activated alkenes.

1. Palladium(0)-catalyzed aryne annulation: a powerful strategy for the synthesis of thio-bridged compounds.

Review 2. Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.