TY  - JOUR
AU  - Gamba, I.
AU  - Gamez, P.
AU  - Monzani, E.
AU  - Casella, L.
AU  - Mutikainen, I.
AU  - Reedijk, J.
T1  - Selective copper-mediated halogenation of aromatic rings under mild conditions
LA  - eng
PY  - 2011
SP  - 4360
EP  - 4368
T2  - European Journal of Inorganic Chemistry
SN  - 1434-1948
AB  - A mild copper-mediated halogenation reaction of phenolic rings is reported. The reaction of bis(2-hydroxybenzyl)-1,3-diaminopropane (H2bhbd) with copper(II) chloride in acetonitrile generates linear trinuclear [Cu 3(bhcbd)2Cl2](CH3CN), containing modified ligands, whose phenol moieties are selectively chlorinated at the 5-position. Under comparable experimental conditions with copper(II) bromide, bromination of the ligand is observed, albeit at a slower reaction rate. In the presence of trialkylorthoformates, which are used as dehydrating agents, a ring closure of the ligand is observed after removal of copper to yield a product with a six-membered ring. This product has been isolated and characterized by NMR spectroscopy and MS. Similarly, bromination of bis(2-hydroxybenzyl)-1,3- diiminopropane (H2bhbdi) occurs in the presence of copper(II) bromide, with concomitant formation of a linear trinuclear complex. Surprisingly, an asymmetric dinuclear copper(II) coordination compound without chlorination of the ligand is obtained when the related ligand bis(2-hydroxybenzyl)-1,3-diminopropane (H2bhbdi) reacts with copper(II) chloride. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
DO  - 10.1002/ejic.201100489
UR  - https://portalciencia.ull.es/documentos/5ee0c2c62999527595f969fc
DP  - Dialnet - Portal de la Investigación
ER  -