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Palladium-Catalyzed Cross-Coupling of 2‑Aryl-1,3-dithianes

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journal contribution
posted on 2014-09-19, 00:00 authored by Summer A. Baker Dockrey, Alicia K. Makepeace, Jason R. Schmink
Palladium-catalyzed cross-coupling of aryl bromides with 2-aryl-1,3-dithianes is described. This methodology takes advantage of the relatively acidic benzylic proton of the dithiane, allowing it to act as a competent, polarity-reversed transmetalation reagent. This unique approach affords the ability to employ an orthogonal deprotection strategy, and practical routes to both diaryl ketones and diarylmethanes are illustrated. Cross-coupling of a range of aryl dithianes with aryl bromides, including scope and current limitations, is presented.