Premium
A Minimalist Approach to CH Activation by Copper
Author(s) -
KuebelPollak Anita,
Rüttimann Stéphane,
Dunn Nichola,
Melich Xavier,
Williams Alan F.,
Bernardinelli Gérald
Publication year - 2006
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200690086
Subject(s) - chemistry , hydroxylation , benzimidazole , ligand (biochemistry) , copper , phenol , medicinal chemistry , benzene , crystal structure , stereochemistry , crystallography , organic chemistry , receptor , enzyme , biochemistry
The complex [Cu 2 ( 1 ) 2 ] 2+ ( 1 = 1,3‐bis(1‐methyl‐1 H ‐benzimidazol‐2‐yl)benzene) undergoes slow oxidation by dioxygen in DMF solution to give the hydroxylated product [Cu 2 ( 2 ‐H) 2 ] 2+ ( 2 = 2,6‐bis(1‐methyl‐1 H ‐benzimidazol‐2‐yl)phenol) characterized by an X‐ray crystal‐structure analysis. The oxidation occurs much faster when Cu II is mixed with 1 in the presence of H 2 O 2 , with 80% hydroxylation observed within a few minutes. The mononuclear complex formed with 1‐methyl‐2‐phenyl‐1 H ‐benzimidazole ( 3 ) shows no hydroxylation under these conditions. It is concluded that the hydroxylation requires the presence of a ligand capable of stabilizing a binuclear species, but no special coordinative activation of the copper is required.