102113-98-4Relevant articles and documents
Probing the Influence of PAd-DalPhos Ancillary Ligand Structure on Nickel-Catalyzed Ammonia Cross-Coupling
Lavoie, Christopher M.,Tassone, Joseph P.,Ferguson, Michael J.,Zhou, Yuqiao,Johnson, Erin R.,Stradiotto, Mark
, p. 4015 - 4023 (2018)
We report herein on the results of our combined experimental/computational study regarding the catalytic performance of PAd-DalPhos (L1) in nickel-catalyzed ammonia arylation for primary aniline synthesis. Primary arylamine C-N reductive eliminations occurring from arylnickel(II) parent amido complexes of the type (L)Ni(Ph)(NH2) were modeled by use of density-functional theory (DFT) methods, for a series of L1 derivatives. The dual aims were to assess the effect of structural modifications to L1 on potentially rate-limiting C-N reductive elimination and to identify promising candidates for experimental inquiry. Increasing the steric demand of the Paryl groups from o-tolyl (in L1) to mesityl (in L16) resulted in a significant lowering of the barrier to C-N reductive elimination (ΔG?RE), which can be attributed in part to interactions between the ligand Paryl groups and the nickel-bound amido ligand, as observed in noncovalent interaction (NCI) plots of the reductive elimination transition-state structures. Despite the favorability of L16 predicted on the basis of computational analysis focusing on C-N reductive elimination, this ancillary ligand performed poorly in experimental testing versus L1, suggesting that in practice the significant steric demands of L16 may discourage the formation of key catalytic intermediates. Modifications to the steric profile of the Paryl groups in L1 led to dramatic changes in catalytic performance, with the presence of an o-methyl proving to be important, among the L1 variants tested, in achieving useful catalytic performance in the Ni-catalyzed monoarylation of ammonia.
DMSO-allyl bromide: A mild and efficient reagent for atom economic one-pot: N -allylation and bromination of 2°-aryl amines, 2-aryl aminoamides, indoles and 7-aza indoles
Kannadasan, Sathananthan,Novanna, Motakatla,Shanmugam, Ponnusamy,Smile, Suresh Snoxma
, p. 1834 - 1839 (2022/02/07)
A mixture DMSO-allyl bromide has been developed as a reagent for an atom economic one-pot N-allylation and aryl bromination under basic conditions. Utilizing this reagent, N-allylation-bromination of a number of 2°-aryl amines, aryl aminoamides, indoles, and 7-aza indoles has been achieved. The scope of the substrates and limitations, the synthetic utility of the products, and a plausible reaction mechanism have been proposed.
Nitrogen-containing compound, electronic component and electronic device
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Paragraph 0154-0160, (2021/01/28)
The application belongs to the field of organic light-emitting materials, and relates to a nitrogen-containing compound, an electronic element and an electronic device. The nitrogen-containing compound has a structure represented by the following formula