Pd/C-catalyzed room-temperature hydrodehalogenation of aryl halides with hydrazine hydrochloride

Tetrahedron Letters

Volumn 44, Issue 38, 2003, Pages 7191-7195

  Cellier, Pascal P ^a   Spindler, Jean Francis ^b   Taillefer, Marc ^a   Cristau, Henri Jean ^a  

^a Laboratoire de Chimie Macromoleculaire UMR 5076   (France)

^b Rhodia Europe   (France)

Author keywords

Aryl halides; Heterogeneous catalysis; Hydrazine; Liquid phase dehalogenation; Palladium catalyst

Indexed keywords

ALLYL COMPOUND; BROMINE DERIVATIVE; CARBON; CHLORINE DERIVATIVE; FLUORINE DERIVATIVE; HALIDE; HYDRAZINE DERIVATIVE; IODINE DERIVATIVE; LEAD; REAGENT; SODIUM HYDROXIDE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; COMBINATORIAL CHEMISTRY; DEHALOGENATION; ELECTRON; ELIMINATION REACTION; HYDROGENATION; OXIDATION REDUCTION REACTION; REDUCTION; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 0041508445     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01789-1     Document Type: Article

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23. Used as 20-40 mesh beads (Aldrich Chem. Co.).
24. Typical procedure: Under an atmosphere of dry and pure nitrogen, an oven-dried Schlenk tube equipped with a magnetic stir bar was charged with 10% w/w Pd/C (26 mg, 0.025 mmol Pd, Fluka), hydrazine hydrochloride (26 mg, 0.375 mmol), sodium hydroxide (40 mg, 1 mmol) and the aryl halide (0.5 mmol), if a solid. The tube was capped with a rubber septum. If a liquid, the aryl halide was added via syringe, followed by anhydrous toluene (1 mL). The septum was removed and the tube was sealed under a positive pressure of nitrogen. The slurry was allowed to stir for 24 h at room temperature. The reaction mixture was then diluted with dichloromethane (5 mL) and a known volume of internal standard was added. A small sample of this mixture was filtered through a plug of Celite®, washed three times with water and analyzed by gas chromatography.
25. No attempts were made to optimize the reduction of dihalogenated aromatics.
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