Pd(II)-catalyzed C–H olefination of aryl 2-pyridyl sulfoxides with unactivated and activated olefins has been demonstrated. We employed environmentally benign and inexpensive molecular oxygen as the sole oxidant. The versatile nature of the 2-pyridyl sulfoxide directinggroup has been proven by its transformation to the sulfone functionality. Deuterium scrambling experiments and intramolecular kinetic