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Heterogeneous Aromatic Amination of Aryl Halides with Arylamines in Water with PS‐PEG Resin‐Supported Palladium Complexes
Author(s) -
Hirai Yoshinori,
Uozumi Yasuhiro
Publication year - 2010
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000192
Subject(s) - amination , aryl , chemistry , palladium , catalysis , polymer chemistry , bromobenzene , ethylene glycol , organic chemistry , phosphine , biphenyl , diphenylamine , phenylboronic acid , alkyl
Catalytic aromatic amination is achieved in water under heterogeneous conditions by the use of immobilized palladium complexes coordinated with the amphiphilic polystyrene‐poly(ethylene glycol) resin‐supported di( tert ‐butyl)phosphine ligand. Aromatic amination of aryl halides with diphenylamine and N,N‐double arylation of anilines with bromobenzene were found to proceed in water with broad substrate tolerance to give the triarylamines in high yield with high recyclability of the polymeric catalyst beads. Very little palladium leached from the polymeric catalyst under the water‐based reaction conditions to provide a green and clean (metal‐uncontaminated) protocol for the preparation of triarylamines, including the optoelectronically active N,N,N′,N′ ‐ tetraaryl‐1,1′‐biphenyl‐4,4′‐diamines (TPDs).