A novel and controllable synthesis of thioacetals/thioketals and β-sulfanyl ketones mediated by the reaction of aldehyde/acetone with thiols has been developed. In this protocol, β-sulfanyl ketones can be generated without the prior preparation of α, β-unsaturated carbonyl compounds. A variety of thiols reacted with aldehyde/acetone and provided the corresponding thioacetals/thioketals and β-sulfanyl ketones in good to excellent yields, respectively. This protocol is operationally simple, mild, and atom-economical, providing controllable access to thioacetals/thioketals and thia-Michael addition products under mild conditions.
Functionalized imidazo[1,2-α]pyridines are important scaffolds in pharmaceuticals. Herein, we present an efficient 3-sulfonylmethylation protocol for imidazo[1,2-α]pyridines by sodium sulfinates in DMA and H2O (2:1) via an FeCl3-catalyzed three-component coupling reaction. Various sulfonylmethyl imidazo[1,2-α]pyridines were thus afforded in high yields with excellent functional group tolerance. A plausible oxidation-addition mechanism was proposed.
β-Keto sulfides are a class of compounds containing both carbonyl (C=O) and thioether (C–S–C) functionalities, exhibiting significant potential in the field of medicinal chemistry. This study employs the silyl enol ether as the substrate, enabling the formation of C–S bonds under catalyst- and additive-free conditions, thereby facilitating the efficient synthesis of β-keto sulfides. The reaction proceeds rapidly and efficiently, exhibiting a broad substrate scope, and a total of 31 target compounds were synthesized with up to 95% yields.