Efficient synthesis of chalcone-4′-sulfonyl chlorides and fluorides

• Published in: Tetrahedron letters Vol. 59; no. 4; pp. 372 - 374
• Main Authors: Semenok, Dmitrii, Kletskov, Alexey, Dikusar, Evgenij, Potkin, Vladimir, Lukin, Oleg
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 24.01.2018; Elsevier
• Subjects: Aldol condensation; Chalcones; Chemistry; Chemistry, Organic; Nucleophilic displacement; Physical Sciences; Science & Technology; Sulfonyl chlorides; Sulfonyl fluorides; Sulfonyl chlorides; Chalcones; Nucleophilic displacement; Sulfonyl fluorides; Aldol condensation
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2017.12.044

[Display omitted] •Synthesis of hitherto unavailable chalcone sulfonyl halides was achieved.•For every condensation case the optimal reaction conditions were developed.•The halogen type and substituents impact the reactivity of the sulfonyl halides. A library of 4′-chloro- and 4′-fluorosulfonyl-substituted chalcones was prepared via the aldol-type condensation reactions of 4-acetylbenzene-1-sulfonyl halides with various aromatic aldehydes, either in absolute ethanol or glacial acetic acid, in the presence of dry HCl. This represents the first examples of chalcone sulfonyl halides in which the phenone ring bears one of these functional groups. The reactivity of the chalcone sulfonyl halides were strongly dependent on the styrene ring substituents; sulfonyl chlorides reacted with most nucleophiles (e.g. amines, alcohols), while sulfonyl fluorides reacted only with charged nucleophiles (e.g. phenolates).