20953-62-2Relevant academic research and scientific papers
Palladium-Catalyzed Animation of Aryl Halides on Solid Support
Weigand, Klaus,Pelka, Sylvie
, p. 4689 - 4692 (2007/10/03)
(Matrix Presented) The first examples of the Pd(0)-catalyzed amination of aryl halides using Rink-resins as nitrogen source are described. Pd2dba3/BINAP/NaO-t-Bu was found to be the most efficient catalyst/base system, while a solvent mixture of dioxane and tert-butyl alcohol was shown to enhance the selectivity toward the desired monoarylation. Moderate to good yields and excellent purities of the amination products were found with electron-poor aryl halides, while electon-rich aryl halides failed to react under these conditions.
Aromatic Nitro group Displacement Reactions. Part 2. The Synthesis of Diarylamines and some Heteroaromatic Analogues.
Gorvin, John H.
, p. 1662 - 1681 (2007/10/02)
In dipolar aprotic solvents, activated aromatic nitro-groups can usually be displaced by anilines of enhanced N-acidity in the presence of the heavier alkali-metal carbonates.When catalysed by potassium t-butoxide, however, attack occurs preferentially at other reactive centers in the molecule, except where the nitro-group is highly activated.Some of the resulting diarylamines (the term is here expanded to include arylaminoxanthen-9-ones) are intermediates in the synthesis of heterocycles.
The Synthesis of Di- and Tri-arylamines through Halogen Displacement by Base-activated Arylamines: Comparison with the Ullmann Condensation
Gorvin, John H.
, p. 1331 - 1336 (2007/10/02)
In dipolar aprotic solvents, nitranions derived from anilines of enhanced N-acidity displace fluorine from activated aromatic compounds at room temperature.Diarylamines thus produced are free from triarylamines, which are formed at higher temperatures when diarylamines, after N-deprotonation by potassium t-butoxyde or by the heavier alkali metal carbonates, similarly displace activated fluorine.Certain diarylamines can also be prepared by chlorine displacement in the presence of alkali metal carbonates.It is confirmed that such carbonates play only an auxiliary role in the Ullmann (copper-assisted) diarylamine synthesis conducted in dipolar aprotic solvents; they may indeed impede the reaction in some instances.
