Efficient palladium-catalyzed amination of aryl chlorides using di(dicyclohexylamino)phenylphosphine as a PN sub(2 ligand)

The palladium-catalyzed amination of a variety of aryl chlorides has been accomplished by using di(dicyclohexylamino)phenylphosphine (1) as a bulky electron-rich monoaryl phosphine ligand. The optimized condition for the palladium-catalyzed amination of aryl chloride is the followings: aniline (3.0...

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Bibliographic Details
Published in:Tetrahedron 2012-01, Vol.68 (1), p.287-293
Main Authors: Kim, Bo Ram, Cho, Su-Dong, Kim, Eun Jung, Lee, In-Hye, Sung, Gi Hyeon, Kim, Jeum-Jong, Lee, Sang-Gyeong, Yoon, Yong-Jin
Format: Article
Language:English
Subjects:
Aromatic compounds
Chlorides
Chlorobenzenes
Couplings
Ligands
Phosphines
Solvents
Toluene
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Summary:The palladium-catalyzed amination of a variety of aryl chlorides has been accomplished by using di(dicyclohexylamino)phenylphosphine (1) as a bulky electron-rich monoaryl phosphine ligand. The optimized condition for the palladium-catalyzed amination of aryl chloride is the followings: aniline (3.0 mmol, 1.0 equiv), chlorobenzene (3.15 mmol, 1.05 equiv), ligand 1 (1 mol %, 0.03 mmol), KO super(tBu (4.5 mmol, 1.5 equiv), Pd) sub(2)(dba) sub(3 (1 mol %, 0.03 mmol), and toluene as solvent at reflux temperature. We report on couplings of various amines or chloroamines with chlorobenzenes and heteroaryl chloride.)
ISSN:0040-4020
DOI:10.1016/j.tet.2011.10.059