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Synthesis of thiochromanones and thioflavanones

Recent Literature

A Rh-catalyzed reaction of β-tert-butylthio-substituted aldehydes and alkynes provides β′-thio-substituted-enones, that smoothly undergo in situ intramolecular S-conjugate addition to deliver a range of S-heterocycles in a one-pot process. Various in situ oxidations are also performed, allowing access to S,S-dioxide derivatives, as well as unsaturated variants.
A. Bouisseau, J. Glancy, M. C. Willis, Org. Lett., 2016, 18, 5676-5679.

In an efficient copper-catalyzed, ligand-free domino process, various 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.
S. Sangeetha, P. Muthupandi, G. Sekar, Org. Lett., 2015, 17, 6006-6009.

An efficient visible light mediated photocatalyst free C-S cross-coupling reaction enables the synthesis of thiochromane and thiochroman-4-ol derivatives through photoinduced electron transfer (PET).
N. Sundaravelu, A. Nandy, G. Sekar, Org. Lett., 2021, 23, 3115-3119.

An iodine-catalyzed denitrative C-S cross-coupling reaction provides thiochromanones from 2′-nitrochalcones and xanthate. The strategy was extended for a three-component synthesis of thiochromenes via intermolecular C-S cross-coupling followed by aldol reaction.
A. Nandy, G. Sekar, J. Org. Chem., 2022, 87, 7536-7546.