Cu-Catalyzed Cross-Coupling of Nitroarenes with Aryl Boronic Acids to Construct Diarylamines.

05 July 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


The development and study of a simple copper-catalyzed reaction of nitroarenes with aryl boronic acids to form diarylamines that uses phenyl silane as the stoichiometric terminal reductant is described. This cross-coupling reaction requires as little as 2 mol % of CuX and 4 mol% of diphosphine for success and tolerates a broad range of functional groups on either the nitroarene or the aryl boronic acid with to afford the amine in good yield. Mechanistic investigations established that the cross-coupling reaction proceeds via a nitrosoarene intermediate and that copper is required to catalyze both the deoxygenation of the nitroarene to afford the nitrosoarene and C–NAr bond formation of the nitrosoarene with the aryl boronic acid.


boronic acids
copper catalysis
diaryl amines
cross coupling reaction

Supplementary materials

Supporting Information
Experimental procedures, characterization data, and spectral information


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