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Palladium‐ and Copper‐Catalyzed Site Selective Monoamination of Dibromobenzoic Acid
Author(s) -
Houpis Ioannis N.,
Weerts Koen,
Nettekoven Ulrike,
Canters Martine,
Tan Hongyu,
Liu Renmao,
Wang Youchu
Publication year - 2011
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.201000800
Subject(s) - chemistry , selectivity , palladium , catalysis , amination , yield (engineering) , copper , carboxylate , aryl , base (topology) , solvent , combinatorial chemistry , organic chemistry , medicinal chemistry , mathematical analysis , materials science , alkyl , mathematics , metallurgy
The carboxylate anion has been used as a directing group in the aromatic amination of electronically equivalent aryl bromides to afford selective ortho ‐substituted derivatives (>99:1 selectivity; 60–80% yield) in the case of copper(I) catalysis. The solvent, base and equivalents of base were important factors in the success of this reaction. Complementary selectivity was achieved with palladium catalysis where the para ‐substituted derivatives were produced selectively (>99% selectivity, 70–80% yield).