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Copper‐Catalyzed Coupling Reactions of Aryl Halides and Phenols by 4,4’‐Dimethoxy‐2,2’‐bipyridine and 4,7‐Dimethoxy‐1,10‐phenanthroline
Author(s) -
Zhao Yingying,
Wang Xiangyong,
Kodama Koichi,
Hirose Takuji
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201802278
Subject(s) - chemistry , aryl , catalysis , ligand (biochemistry) , phenols , medicinal chemistry , halide , yield (engineering) , bipyridine , phenanthroline , coupling reaction , denticity , 2,2' bipyridine , organic chemistry , metal , crystal structure , alkyl , materials science , biochemistry , receptor , metallurgy
Several Cu(I) complexes of 2,2’‐bipyridines were studied for the catalytic coupling of aryl iodides and phenols and 4,4’‐dimethoxy‐2,2’‐bipyridine was shown to be an effective ligand of CuI in 1:2 (CuI:ligand) ratio for the synthesis of a wide range of diaryl ethers (up to 97% yield) using K 3 PO 4 as base in DMF at 100 °C. The catalysis was highly dependent on the reaction temperature and was successfully applied in the coupling with more attractive and challenging substrates, aryl bromides, at 140 °C in good‐to‐excellent yields (78−95%). Moreover, the heteroaromatic effect for the reaction was studied and gave a comparable result with phenyl group (up to 95% yield). Significantly, a structurally related N , N ‐bidentate ligand, 4,7‐dimethoxy‐1,10‐phenanthroline, exhibited better performance for less‐reactive combinations of aryl halides and phenols.