Science of Synthesis

Gagnon, A.; Benoit, E.; Le Roch, A., Science of Synthesis Knowledge Updates, (2018) 4, 78.

Very few examples of S-arylation reactions using organobismuth reagents have been reported. The phenylation of a small number of arenethiols was performed in good to excellent yield using triphenylbismuth(V) carbonate;[‌310‌] however, because thiols have a propensity to form diaryl disulfides, S-arylation methods involving organobismuthines have been developed directly from diaryl disulfides. Thus, reaction of diaryl disulfides ‌168‌ with triarylbismuthines and copper(I) acetate in the presence of 1,10-phenanthroline in dimethyl sulfoxide at 100 °C under air affords the corresponding diaryl thioethers ‌169‌ in good to excellent yields (‌Scheme 93‌).[‌347‌] Interestingly, and contrary to other copper-catalyzed arylation reactions using triarylbismuthines, more than one aryl group is transferred from the organobismuth reagent.

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