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Copper Complexes as Functional Models for Dopamine β‐Hydroxylase – Stereospecific Oxygen Atom Transfer
Author(s) -
Blain Ingrid,
Bruno Pascale,
Giorgi Michel,
Lojou Elisabeth,
Lexa Doris,
Réglier Marius
Publication year - 1998
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/(sici)1099-0682(199809)1998:9<1297::aid-ejic1297>3.0.co;2-m
Subject(s) - chemistry , copper , stereospecificity , oxygen , ligand (biochemistry) , kinetic isotope effect , benzoin , photochemistry , deuterium , inorganic chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , physics , receptor , quantum mechanics
The stereochemistry of oxygen atom transfer mediated by copper–oxygen species has been studied through a substrate binding ligand approach. Copper(II) [(IndPY2)Cu](CF 3 SO 3 ) 2 ( 2a ) and copper(I) [(IndPY2)Cu]PF 6 ( 5a ) complexes were prepared and exposed to O 2 in media of benzoin/NEt 3 /CH 2 Cl 2 and CH 2 Cl 2 , respectively. In both cases, highly regio‐ and stereoselective oxygen atom transfer to the benzylic C–H bond of the indane ligand occurred. Using deuterium‐labelled copper complexes 2b and 5b , we found that, in both cases, the oxygen atom transfer occurs with retention of configuration. The high deuterium kinetic isotope effects (7.6 and 11, respectively), determined by 13 C‐NMR spectroscopy, strongly suggest the intermediacy of two different copper–oxygen reactive species.