A copper-catalyzed sulfinyl cross-coupling reaction of sulfinamides with aldehyde-derived N -tosylhydrazones is described. This approach enables facile access for the construction of structurally diverse sulfoxides via novel and efficient S-N/S-C bond interconversions, features broad substrate scope, and accommodates various functional groups as well as pharmacophores. Moreover, the given sulfinyl cross-coupling reaction could be scaled up to the gram scale and carried out in a one-pot fashion directly from aldehydes. The broad utility of produced sulfoxides is demonstrated by further transformations. A preliminary mechanistic investigation was performed, which disclosed possible reaction pathways.