Abstract
A novel domino reaction from benzaldehydes and 2-acetylfuran/2-acetylthiophene with sodium sulfide was developed to synthesize a series of tetrahydrothiopyran (THTP) derivatives. The reaction proceeded well to construct a tetrahydrothiopyran ring and five new bonds in one step. A mechanism is proposed, involving a stepwise Aldol/double Michael addition/Aldol (AMMA) reaction cascade. In this transformation, sodium sulfide acts as a nucleophile and base. This method is characterized by transition-metal-free, commercially available starting materials and mild reaction conditions.
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