53884-32-5Relevant articles and documents
Formal arylation of NH3 to produce diphenylamines over supported Pd catalysts
Koizumi, Yu,Taniguchi, Kento,Jin, Xiongjie,Yamaguchi, Kazuya,Nozaki, Kyoko,Mizuno, Noritaka
supporting information, p. 10827 - 10830 (2017/10/09)
In the presence of supported Pd nanoparticle catalysts, e.g., Pd/Al2O3, various diphenylamines could be synthesized through acceptorless formal arylation using NH3 or its surrogates, e.g., urea, as nitrogen sources and cyclohexanones as arylation sources. The observed catalysis was truly heterogeneous, and the catalyst was reusable with retention of its high catalytic performance.
Palladium-catalyzed coupling of ammonia with aryl chlorides, bromides, iodides, and sulfonates: A general method for the preparation of primary arylamines
Vo, Giang D.,Hartwig, John F.
supporting information; experimental part, p. 11049 - 11061 (2009/12/05)
We report that the complex generated from Pd[P(o-tol)3] 2 and the alkylbisphosphine CyPF-t-Bu is a highly active and selective catalyst for the coupling of ammonia with aryl chlorides, bromides, iodides, and sulfonates. The couplings of ammonia with this catalyst conducted with a solution of ammonia in dioxane form primary arylamines from a variety of aryl electrophiles in high yields. Catalyst loadings as low as 0.1 mol % were sufficient for reactions of many aryl chlorides and bromides. In the presence of this catalyst, aryl sulfonates also coupled with ammonia for the first time in high yields. A comparison of reactions in the presence of this catalyst versus those in the presence of existing copper and palladium systems revealed a complementary, if not broader, substrate scope. The utility of this method to generate amides, imides, and carbamates is illustrated by a one-pot synthesis of a small library of these carbonyl compounds from aryl bromides and chlorides, ammonia, and acid chlorides or anhydrides. Mechanistic studies show that reactions conducted with the combination of Pd[P(o-tol)3]2 and CyPF-t-Bu as catalyst occur with faster rates and higher yields than those conducted with CyPF-t-Bu and palladiun(II) as catalyst precursors because of the low concentration of active catalyst that is generated from the combination of palladium(II), ammonia, and base.
Inverse Triphenylmethylium Dyes
Hellwinkel, Dieter,Gaa, Heinrich Georg,Gottfried, Reiner
, p. 1045 - 1060 (2007/10/02)
When in the conventional triphenymethylium dye systems of the crystal violet and malachit green type, 6 and 7, the N-donor and C(+)-acceptor centers are interchanged, the "Inverse Triphenylmethylium Dye Types" 4 and 5 are obtained, showing very similar colors.The stable models with R = phenyl (8 - 10) and R = p-tolyl (11 - 13) were investigated in more detail.The visual observations were supported by the VIS spectra which showed nearly the same longest wavelength absorption maxima for corresponding pairs of inverse and conventional dye representatives.The experimental results can be interpreted with a simple HMO-model according to which the longest wavelength absorptions correspond here to transitions of equal energy from weakly bonding to nonbonding and from nonbonding to weakly antibonding molecular orbitals, respectively.On the same basis numerous isoelectronic variants of that dye type can be envisaged.In the NMR-spectra of the new dyes, characteristically increasing deshieldings of nearly all positions are observed in going from the mono- (10(+), 13(+)) through the di- (9(++), 12(++)) to the trications (8(+++), 11(+++)). - Key words: Dyes, Di-, Tricarbeniumions, NMR Spectra, VIS Spectra
