37055-23-5Relevant academic research and scientific papers
Reactions of Alkyl-lithium Compounds with Aryl Halides
Huddle, Penelope A.,Perold, Guido W.
, p. 2617 - 2625 (2007/10/02)
Reation of methyl-lithium with tribromophenols and with other aryl polyhalides leads directly to bi- and tri-aryl products. para-Substituents (Y) of 2,6-dibromo-4-Y-phenols promote arylation of substrates by their own lithiation products as Y becomes more electron-withdrawing.An aryne epoxide is not an intermediate in these reactions. 2,4,6-Tribromo-Z-benzenes react to form coupling products when Z can co-ordinate to an introduced ortho-lithium atom or when Z can be directly lithiated.Dimeric aggregation of the organolithium intermediates occurs so as to favor coupling to halogenated substrates.Both polar (ionic) and free-radical pathways are involved.
