Nitroalkanes are highly valuable synthetic intermediates, owing to their unique reactivity and diverse range functional group transformations.  Despite this utility, access to these compounds remains synthetically challenging.  An efficient palladium-catalyzed coupling of aryl halides with inexpensive nitromethane has been developed that affords the product arylnitromethanes in high yield and with good functional group tolerance.  Exploiting the use of nitromethane as a formyl equivalent, an efficient direct conversion of the arylnitromethanes to the corresponding oxime and aldehyde has been developed.  Notably, these reactions can be combined affording a one-pot transformation of an aryl halide to the aryl aldehyde or aryl oxime in good yield.  This method allows for a mild alternative to electrophilic aromatic formylation, lithiation protocols, and aryl halide carbonylation.

Palladium-catalyzed nitromethylation of aryl halides: Use of nitromethane as a formyl equivalent

244th National Meeting (2012)

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