Complexes of Copper(I) with Aromatic Compounds
facilitate Selective Electrophilic and Nucleiophilic
MAGAL SAPHIER1,2, Israel Zilbermann1, Ariela Burg2, Oshra Saphier2
1 - Chemistry, N.R.C.N, Beer Shiva, Israel
2 - Chemistry Engineering, Sami Shamoon College of Engineering, Beer Shiva, Israel
Complexes of Copper(I) with aromatic compounds in aqueous solutions have been studied in the
past and the stability constants of Cu(I)-Phenol in aqueous solutions found to be 900 + 100 .
The surprisingly stable d * Cu(I)-phenol complexes causing distortion of the ring structure
facilitates selective substitutions 
The complex Cu(I)-phenol in aqueous solutions reacts at room temperature whit diluted nitric acid
to selectively form Ortho-nitrophenol and with ammonia to selectively form Ortho-aminophenol
. The complex of copper(I) with Phenol was formed in sit from Cu(II) and metal copper in
deaerated aqueous solutions containing Phenol. The Phenol shifted the dispoportionation reaction
to the formation of Cu(I):
(aqueous Phenol)Cu2++ Cuo (s) 2Cu+ (Phenol)
This finding corroborate previous results mechanism proposed for Ullmann reaction involves the
formation of [Cu(I)- Aromatic ring] intermediate in first stage .
The reactions were monitored by HPLC and UV-Vis spectroscopy .
1. Saphier M., Burg A., Sheps S., Cohen H., Meyerstein D., Complexes of
copper (1) with aromatic compouns in aqueous solutions. J. Chem. Soc.,
Dalton Trans., 1999, 1845-1849.
2. Saphier M., Massarwa A., Cohen H., Meyerstein D., Copper(I) as
Homogeneos Catalyst for the Ullmann Reaction in Aqueous Solutions- The
Transformation of 2-Bromobenzoate in to Salicylate., Eur. J. Inorg. Chem.,
3. Saphier M, PCT /IL2009/001099, WO/2010/061382, International Filing
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