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A new, convenient, and efficient method for the synthesis of homoallylic aromatic thioethers was developed. The present method consists of the formation of arylthionium intermediates from aromatic dithioacetals, which are trapped by a π-nucleophile. Screening of diverse aromatic substrates, selected Lewis acids, and allylstannane and allylsilane were evaluated. The method was found suitable for the preparation of homoallylic aryl thioethers bearing electron donating o- and p-groups only, as substrates with electron withdrawing groups were found unreactive to this system.

Convenient method to obtain homoallylic thioethers from aromatic dithioacetal derivatives