The reduction of nitroarenes followed by the arylation of the resulting amine is one of the most common synthetic sequences in medicinal chemistry, due to the utility of nitro group’s directing and activating properties on arenes and their ease of installation. One attractive alternative to this approach is the direct, reductive arylation of nitroarenes. Herein, we describe the development of a reaction that employs a commonly available palladium catalyst to directly arylate a variety of nitroarenes and nitroheteroarenes with various chloroarenes. This method obviates the need for either a discrete reduction step or the use of carbon-based nucleophiles, such as boronic acids, when synthesizing diarylamines. Preliminary mechanistic investigations indicate that the palladium catalyst is necessary for both the nitroarene semi-reduction and the arylation of an intermediate azoarene.

Palladium-catalyzed reductive formation of C-N bonds from nitroarenes and aryl chlorides

ACS Spring Meeting 2021

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