31084-57-8Relevant academic research and scientific papers
A comparative reactivity survey of some prominent bisphosphine nickel(II) precatalysts in C-N cross-coupling
Clark, Jillian S. K.,Lavoie, Christopher M.,MacQueen, Preston M.,Ferguson, Michael J.,Stradiotto, Mark
, p. 3248 - 3254 (2016)
The synthesis and characterization of the new air-stable precatalyst (L1)Ni(o-tol)Cl (C1; where L1 = JosiPhos CyPF-Cy) is reported, along with the results of a comparative reactivity survey involving C1 and analogous PAd-DalPhos- and DPPF-containing precatalysts (C2 and C3, respectively) in representative nickel-catalyzed C(sp2)-N cross-coupling reactions. Precatalyst C1 was found to be competitive with, and in some cases complementary to, C2 in the monoarylation of ammonia and primary alkylamines with (hetero)aryl chlorides, including in otherwise challenging room temperature transformations. (Pseudo)halide comparison studies involving the cross-coupling of furfurylamine at room temperature revealed that in contrast to C2 precatalyst C1 performs less effectively with aryl bromides. Whereas C3 was found to be ineffective for such transformations, this DPPF-derived precatalyst proved superior to C1 and C2 in reactions involving the secondary dialkylamine test substrate morpholine.
[(CyPF-Bu)PdCI2]: An air-stable, one-component, highly efficient catalyst for amination of heteroaryl and aryl halides
Shen, Qilong,Hartwig, John F.
supporting information; experimental part, p. 4109 - 4112 (2009/05/27)
(Chemical Equation Presented) An air- and moisture-stable palladium catalyst, [(CyPF-1Bu)PdCI2] (1), for coupling of heteroaryl chlorides, bromides, and iodides with a variety of primary amines is described. Most of these reactions occurred in high yield with 0.001-0.05 mol % catalyst loading. The reactions tolerated a wide range of functional groups.
Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates
Wolfe, John P.,Tomori, Hiroshi,Sadighi, Joseph P.,Yin, Jingjun,Buchwald, Stephen L.
, p. 1158 - 1174 (2007/10/03)
Palladium complexes supported by (o-biphenyl)P(t-Bu)2 (3) or (o- biphenyl)PCy2 (4) are efficient catalysts for the catalytic amination of a wide variety of aryl halides and triflates. Use of ligand 3 allows for the room-temperature catalytic amination of many aryl chloride, bromide, and triflate substrates, while ligand 4 is effective for the amination of functionalized substrates or reactions of acyclic secondary amines. The catalysts perform well for a large number of different substrate combinations at 80-110 °C, including chloropyridines and functionalized aryl halides and triflates using 0.5-1.0 mol % Pd; some reactions proceed efficiently at low catalyst levels (0.05 mol % Pd). These ligands are effective for almost all substrate combinations that have been previously reported with various other ligands, and they represent the most generally effective catalyst system reported to date. Ligands 3 and 4 are air-stable, crystalline solids that are commercially available. Their effectiveness is believed to be due to a combination of steric and electronic properties that promote oxidative addition, Pd-N bond formation, and reductive elimination.
