‘Awaken’ aryl sulfonyl fluoride: a new partner in the Suzuki–Miyaura coupling reaction

Abstract

An example of the activation of the –SO₂F group, which is traditionally considered a stable group even in the presence of a transition metal, is described using a novel partner in the Suzuki–Miyaura coupling reaction catalyzed by Pd(OAc)₂ and Ruphos as ligands. The products showed good to outstanding yields and broad functional group compatibility under optimal conditions. The sequential synthesis of non-symmetric terphenyls and the gram grade process highlight the approach's synthetic utility. DFT calculations have shown that Pd⁰ prefers to insert between C–S bonds rather than S–F bonds.