Heterogeneous C-N coupling of bromobenzene with aniline has been investigated in flow conditions, with the emphasis on the kinetic evolution of the catalyst (1 % Cu 2 O/support) deactivation. A kinetic model including parallel and sequential steps leading to the formation of three reaction products (diphenylamine, triphenylamine and aminodiphenyl) has been established. It was found that the support is not inert in this reaction and changing its composition induced the following order of the catalytic activity: 1 % Cu 2 O/Al 2 O 3 > 1 % Cu 2 O/TiO 2 > 1 % Cu 2 O/ZnO. Conversely, the resistance to deactivation varied in the reverse order. This was merely assigned to the nature of the interaction of copper with the catalyst support. Among them, Cu 2 O/TiO 2 highlighted the best compromise between the catalytic activity and the resistance to deactivation. It was also found that a larger excess of aniline improved the selectivity in diphenylamine and enhanced the catalyst (1 % Cu 2 O/TiO 2 ) resistance to deactivation. Structural characterization of these catalysts by XRD, XPS and H 2 -TPR provided support for the evidenced kinetic results.