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Copper-Catalyzed Domino Synthesis of 2-Arylthiochromanones through Concomitant C-S Bond Formations Using Xanthate as
Subramani Sangeetha1, Pandi Muthupandi1, Govindasamy Sekar1
1Department of Chemistry, Indian Institute of Technology Madras , Chennai 600036, Tamil Nadu, India.
Abstract:
An efficient domino process for the synthesis of thioflavanones has been described using a copper catalyst without addition of any external ligand. A variety of thioflavanones have been synthesized from easily accessible 2'-iodochalcones or 2'-bromochalcones in excellent yield through in situ incorporation of sulfur using xanthate as an odorless sulfur source. This domino process proceeds through Cu-catalyzed C(aryl)-S bond formation by the coupling reaction of xanthate with 2'-halochalcones followed by C-S bond cleavage of thioester then S-C bond formation by intramolecular Michael addition.
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