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Homocoupling of aryl halides promoted by an NiCl 2 /bpy/Mg system in DMF
Author(s) -
Yamamoto Takakazu
Publication year - 2014
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3168
Subject(s) - arylene , chemistry , halide , aryl , bromide , conjugated system , medicinal chemistry , polymer chemistry , aryl halide , organic chemistry , polymer , alkyl
Homocoupling of aryl halides (2 ArX → Ar―Ar) promoted by NiCl 2 /2,2′‐bipyridine (bpy)/Mg mixtures in DMF has been studied. Mixtures of NiCl 2 , bpy and Mg in DMF promoted homocoupling of aryl halides such as phenyl bromide and p ‐tolyl bromide to give the coupling products in good (e.g. approximately 60–75%) yields, and the homocoupling products were easily isolated from the reaction mixtures. Application of this homocoupling to dibromo‐aromatic compounds (Br–arylene–Br: 2,5‐dibromopyridine, 2,7‐dibromo‐9.9‐dioctylfluorene and 2,7‐dibromo‐9,10‐dioctyl‐9,10‐dihydrophenanthrene) gave the corresponding π‐conjugated polymers, –(arylene) n –, in good yields. Organometallic processes for the homocoupling are discussed. Copyright © 2014 John Wiley & Sons, Ltd.