Synthetic methods for oxidative aromatic C-O bond formation are sparse, despite their demand in metabolite synthesis for drug discovery and development. We report a novel methodology for late-stage C-O bond formation of arenes. The reaction proceeds with excellent functional group tolerance even for highly functionalized substrates. The resulting aryl mesylates provide access to potential human metabolites of pharmaceuticals, and may be used directly to install a C-F bond to block metabolic hotspots. A charge-transfer interaction between the reagent bis(methanesulfonyl) peroxide and the substrate arenes may be relevant for the chemoselective functionalization of arenes over other functional groups.
PROCESS FOR PREPARING BIS(ALKANESULFONYL PEROXIDE)
A process for preparing bis(alkanesulfonyl)peroxide of the formula (I), in which ALK represents an alkyl group, characterized by the following process steps: a)mixing an alkylsulfonic acid chloride in a reaction vessel; b)with an excess of a peroxide-containing compound; c)optionally adding a basic compound if hydrogen peroxide is employed; d)allowing the mixture to react; adding water to terminate the reaction; and e)separating the reaction product obtained, bis(alkanesulfonyl)peroxide.
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(2015/06/03)
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