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We describe conditions under which aryl sulfones act as electrophilic coupling partners in the palladium-catalyzed Suzuki–Miyaura cross-coupling (SMC) reaction. Sequential cross-coupling of arenes bearing sulfone, halide and nitro leaving groups permits rapid access to non-symmetric terphenyls and quaterphenyls starting from common functional groups. Mechanistic experiments and DFT calculations are consistent with oxidative addition into the sulfone C–S bond as the turnover-limiting step.