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Palladium-catalyzed C-H thiolation of aryl 2-pyridyl sulfoxide with diaryl disulfides has been achieved. The reaction proceeds selectively at the ortho-position of masked thiophenol. The directing group 2-pyridyl sulfoxide can be...

Pd(II)-catalyzed C-H olefination of aryl 2-pyridyl sulfoxide with unactivated and activated olefins have been demonstrated. We employed environmentally benign and less expensive molecular oxygen as the sole oxidant. The versatile nature of the 2-pyridyl sulfoxide directing group has been proven by transforming into sulfone functionalities. Deuterium scrambling experiments and intramolecular kinetic isotopic studies were carried out to gain insights into the reaction pathway.