Journal of Organic Chemistry p. 3162 - 3165 (1986)
Update date:2022-07-31
Topics:
Du, Chi-Jen Frank
Hart, Harold
Ng, Kwok-Keung Daniel
Aryl-Grignards (3+ equiv) react with 2,6-dibromoiodobenzene or other 1,2,3-trihalobenzenes to give 2,6-diarylphenylmagnesium halides.The mechanism involves Grignard exchange at the central halogen, followed by two cycles of magnesium halide loss and regioselective capture of the resulting aryne by the aryl-Grignard reagent (Scheme I).Typical examples are shown in Table I.The method is especially applicable to m-terphenyls in which the "outer" rings are identical and/or in which substitution at the 2' or other positions of the "central" ring is desired.
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