Synthesis of 2-aryl benzoxazoles and aryl sulfoxide derivatives in a one-pot process has been developed via the palladium-catalyzed cross-coupling of diaryl sulfoxides with benzoxazoles, followed by trapping the remaining sulfenate anions with different electrophilic reagents. The reaction involves the C-S and C-H bond activation and the C-C and C-S bond formation. The protocol allows a broad scope of substrates, functional group tolerance, and scalability.