19287-65-1Relevant academic research and scientific papers
A tuned bicyclic proazaphosphatrane for catalytically enhanced n-arylation reactions with aryl chlorides
Kim, So Han,Kim, Min,Verkade, John G.,Kim, Youngjo
, p. 1954 - 1960 (2015/03/18)
The N-arylation of various amines with aryl chlorides proceeded in good-to-excellent yields in the presence of P[N{(p-NMe2)C6H4CH2}CH2CH2]3N (1e, a new electron-rich proazaphosphatrane ligand) and small amounts of Pd2(dba)3 (dba = dibenzylideneacetone). This catalytic system was also very effective for the synthesis of carbazoles. An efficient palladium-catalyzed N-arylation reaction of amines under mild conditions with a tuned bicyclic proazaphosphatrane has been developed.
Synthesis of heteroaromatic derivatives with nitrogen atoms: Tripyrrolyl pyrimidine and tripyrrolyl[1,3,5]triazine
Lee,Lee,Jung,Hahn
, p. 501 - 504 (2013/02/22)
As a part of a research program related to the synthetic study of pharmacologically and photoconductively interesting pyrrole derivatives, we have synthesized 1-arylpyrroles (3a-e), 9-arylcarbazoles (4a-e), aminophenylpyrroles (6a,b), dipyrrolylbenzenes (7a-c), 2,4,6-tri-pyrrol-1- yl-pyrimidine (8) and 2,4,6-tri-pyrrol-1-yl[1,3,5]triazine (9). We proposed a plausible mechanism for the formation of 9-arylcarbazole.
Palladium-catalyzed synthesis of N-arylated carbazoles using anilines and cyclic diaryliodonium salts
Riedmueller, Stefan,Nachtsheim, Boris J.
, p. 1202 - 1209 (2013/07/26)
The direct synthesis of N-arylated carbazoles through a palladium-catalyzed amination of cyclic iodonium salts with anilines is described. In particular, electron-poor aniline derivatives reacted smoothly with only 5 mol % of Pd(OAc)2 as catalyst to give the desired products in up to 71% yield. Furthermore, the reactivity of cyclic iodonium salts is compared with the reactivity of the corresponding cyclic bromonium analogues.
Highly efficient ligands for the palladium-assisted double N-arylation of primary amines for one-sep construction of carbazoles
Zhou, Yibo,Verkade, John G.
supporting information; experimental part, p. 616 - 620 (2010/07/03)
A highly efficient one-pot synthesis of carbazoles via palladium-catalyzed double N-arylation of primary amines with 2,2'-dihalobiphenyls is described using a catalyst system comprised of tris(dibenzylideneacetone)dipalladium(O) (Pd2dba3) and the proazaphosphatrane P(i-BuNCH 2CH2)3N (8) or its derivative (t-Bu) 2P=N-P(iBuNCH2CH2)3N (9a) as the ligand. The process is effective for double N-arylation of 2,2'-biphenyl dibromide, diiodide, and even dichloride with a variety of primary amines including neutral, electronrich, electron-deficient, and sterically hindered anilines as well as aliphatic amines.
