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Copper‐Catalyzed Oxybromination and Oxychlorination of Primary Aromatic Amines Using LiBr or LiCl and Molecular Oxygen
Author(s) -
Menini Luciano,
da Cruz Santos Joyce C.,
Gusevskaya Elena V.
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800223
Subject(s) - chemistry , chemoselectivity , aniline , catalysis , primary (astronomy) , bromide , regioselectivity , copper , organic chemistry , oxygen , combinatorial chemistry , physics , astronomy
Nuclear oxybromination of unprotected aromatic primary amines catalyzed by copper(II) acetate [Cu(OAc) 2 ] under mild conditions has been developed, in which bromide ions are used as halogenating agents and dioxygen as a final oxidant. The catalyst shows not only high regioselectivity for para ‐ or ortho ‐isomers but also a remarkable chemoselectivity for monobromination. Oxychlorination of aniline can also be performed under similar conditions, albeit with lower selectivities, with N ‐phenylacetamide being the main by‐product. This simple catalytic method represents ecologically benign and economically attractive synthetic pathway to expensive low‐volume aromatic haloamines.