Key points are not available for this paper at this time.
A Ru(II)-catalyzed straightforward and efficient strategy has been developed to construct O -alkylated arylnaphthyl thioether derivatives using arylthioacetates/arylalkylthioethers with diazonaphthoquinone via a 1,4- oxa sigmatropic rearrangement. In a complementary method, heteroaryl thioacetate/heteroaryl alkylthioethers offer O -heteroaryl alkylnaphthyl thioether derivatives via an interesting concerted intramolecular S N Ar-type reaction. Both of these methods proceed through the formation of Ru-based quinoid carbene and sulfur ylide, respectively. A detailed mechanistic study and DFT calculations reveal that the reaction is going via a concerted manner. Postsynthetic modifications of the synthesized compounds led to sulfur-containing polyaromatic heterocycles.
Pan et al. (Mon,) studied this question.