- N-Arylation of aliphatic, aromatic and heteroaromatic amines catalyzed by copper bis(2,2,6,6-tetramethyl-3,5-heptanedionate)
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Copper bis(2,2,6,6-tetramethyl-3,5-heptanedionate) was found to be an efficient catalyst for N-arylation of aliphatic, aromatic and heteroaromatic amines with aryl iodides/bromides under mild conditions. The system tolerated a variety of hindered and functionalized amines/aryl halides and the desired N-aryl amines were obtained in good to excellent yields.
- Nandurkar, Nitin S.,Bhanushali, Mayur J.,Bhor, Malhari D.,Bhanage, Bhalchandra M.
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- Clean synthesis of triarylamines: Buchwald-Hartwig reaction in water with amphiphilic resin-supported palladium complexes
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Catalytic aromatic amination was achieved in water under heterogeneous conditions by the use of palladium complexes anchored to the amphiphilic PS-PEG resin with little palladium leaching 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).
- Hirai, Yoshinori,Uozumi, Yasuhiro
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supporting information; experimental part
p. 1103 - 1105
(2010/06/18)
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- Heterogeneous aromatic amination of aryl halides with arylamines in water with PS-PEG resin-supported palladium complexes
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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 waterbased 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).
- Hirai, Yoshinori,Uozumi, Yasuhiro
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supporting information; experimental part
p. 1788 - 1795
(2011/04/16)
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- Mechanism and Models for Copper Mediated Nucleophilic Aromatic Substitution. 2. A Single Catalytic Species from Three Different Oxidation States of Copper in an Ullmann Synthesis of Triarylamines
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Ullmann condensations of diarylamines with iodobenzenes has been investigated under homogeneous and a heterogeneous catalytic conditions with cupruos and cupric salts, as well as powered copper metal.Copper catalyzed condensation of diarylamines with iodoaromatics is relatively insensitive to substituent (for substituted iodobenzenes p=-0.25; for substituted diphenylamines p=1.09) but quite sensitive to halogen (k1/kBr.200).The first direct evidence for solution catalysis after filtration of a metal catalyzed reactions was obtained.Quantitative analysis of reaction rates, product yields, and catalyst characteristics leads to a comprehensive picture of the formation of soluble cuprous ions as the single active catalytic species under all conditions investigated.This hypothesis rationalizes many of the perplexing results which typify the literature associated with copper catalyzed nucleophilic aromatic substitution.
- Paine, Anthony James
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p. 1496 - 1502
(2007/10/02)
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