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Efficient Copper‐Catalyzed Synthesis of N ‐Alkylanthranilic Acids via an ortho ‐Substituent Effect of the Carboxyl Group of 2‐Halobenzoic Acids at Room Temperature
Author(s) -
Zeng Liang,
Fu Hua,
Qiao Renzhong,
Jiang Yuyang,
Zhao Yufen
Publication year - 2009
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.200900065
Subject(s) - chemistry , copper , catalysis , substituent , iodide , diol , ligand (biochemistry) , combinatorial chemistry , organic chemistry , medicinal chemistry , biochemistry , receptor
We have developed an efficient copper‐catalyzed method for the synthesis of N ‐alkylanthranilic acids. The protocol uses inexpensive copper(I) iodide/racemic 1,1′‐binaphthyl‐2,2′‐diol ( rac ‐BINOL) as the catalyst/ligand system, readily available 2‐halobenzoic acids and aliphatic amines as the starting materials, the coupling reactions were performed at room temperature, and various functionalities in the substrates were tolerated.