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Base-Catalyzed Aryl Halide Isomerization Enables the 4-Selective Substitution of 3-Bromopyridines
preprintsubmitted on 24.03.2020, 23:57 and posted on 25.03.2020, 12:46 by Thomas R. Puleo, Jeffrey Bandar
The base-catalyzed isomerization of simple aryl halides is presented and utilized to achieve the 4-selective etherification, hydroxylation and amination of 3bromopyridines. Mechanistic studies support isomerization of 3-bromopyridines to 4-bromopyridines proceeds via pyridyne intermediates and that 4-substitution selectivity is driven by a facile SNAr reaction. Beneficial aspects of a tandem aryl halide isomerization/selective interception approach to aromatic functionalization are demonstrated.
Read the published paper
in Chemical Science