Wang, Justin Y. published the artcileCross-Coupling between Hydrazine and Aryl Halides with Hydroxide Base at Low Loadings of Palladium by Rate-Determining Deprotonation of Bound Hydrazine, Application In Synthesis of 452-63-1, the main research area is hydrazine aryl halide cross coupling palladium catalyst hydroxide base; safety hydrazine toxic explosive; amination; cross-coupling; palladium; reaction mechanisms; synthetic methods.
Reported here is the Pd-catalyzed C-N coupling of hydrazine with (hetero)aryl chlorides and bromides to form aryl hydrazines with catalyst loadings as low as 100 ppm of Pd and KOH as base. Mechanistic studies revealed two catalyst resting states: an arylpalladium(II) hydroxide and arylpalladium(II) chloride. These compounds are present in two interconnected catalytic cycles and react with hydrazine and base or hydrazine alone to give the product. The selectivity of the hydroxide complex with hydrazine to form aryl over diaryl hydrazine was lower than that of the chloride complex, as well as the catalytic reaction. In contrast, the selectivity of the chloride complex closely matched that of the catalytic reaction, indicating that the aryl hydrazine is derived from this complex. Kinetic studies showed that the coupling process occurs by rate-limiting deprotonation of a hydrazine-bound arylpalladium(II) chloride complex to give an arylpalladium(II) hydrazido complex. Hydrazine is highly toxic and should be handled with proper personal protection equipment. Hydrazine can also explode in the presence of elevated temperatures and oxygen, and this reaction is catalyzed by transition metals.
Angewandte Chemie, International Edition published new progress about Aryl bromides Role: RCT (Reactant), RACT (Reactant or Reagent). 452-63-1 belongs to class bromides-buliding-blocks, name is 1-Bromo-4-fluoro-2-methylbenzene, and the molecular formula is C7H6BrF, Application In Synthesis of 452-63-1.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary