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Optimization of the Conditions for Copper‐Mediated N ‐Arylation of Heteroarylamines
Author(s) -
Liu Yifeng,
Bai Yajun,
Zhang Juan,
Li Yangyang,
Jiao Junping,
Qi Xiaoli
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700577
Subject(s) - chemistry , copper , ligand (biochemistry) , nucleophile , aryl , catalysis , base (topology) , solvent , coupling reaction , medicinal chemistry , reaction conditions , combinatorial chemistry , polymer chemistry , organic chemistry , receptor , mathematical analysis , biochemistry , alkyl , mathematics
Simple and inexpensive copper‐mediated N ‐arylation ofheteroarylamines was achieved by using N , N ′‐dimethylethylenediamine as a ligand and K 2 CO 3 as a base in dioxane heated at 100 °C. In this coupling reaction, the influence of the copper species, ligand, base and solvent was investigated in detail. N ‐Arylated derivatives of several heteroarylamines were synthesized under optimized reaction conditions, and all the products were isolated in good yields. By controlling the amount of CuI/DMEDA added, heteroarylamines with weak nucleophilic activity were coupled with aryl iodides or aryl bromides. The activity of the copper catalyst for this C–N bond‐forming reaction follows the order Cu I > Cu 0 > Cu II . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
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