Visible-light-promoted one-pot synthesis of β-keto sulfones from aryldiazo tetrafluoroborate salts via aerobic multicomponent reaction

• Published in: Tetrahedron Vol. 167; p. 134303
• Main Authors: Luu, Truong Giang, Kim, Hee-Kwon
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 07.11.2024
• Subjects: Aryl diazonium; DABSO; Multicomponent reaction; Visible-light-induced-reaction; β-Keto sulfones; β-Keto sulfones; Multicomponent reaction; Visible-light-induced-reaction; Aryl diazonium; DABSO
• ISSN: 0040-4020
• DOI: 10.1016/j.tet.2024.134303

β-Keto sulfone is a useful structure in organic chemistry and pharmaceuticals. In the present study, we developed a highly efficient visible-light-promoted reaction to prepare β-keto sulfones under mild conditions. Synthesis was achieved via one-pot multi-component reaction of aryldiazo tetrafluoroborate salts, alkenes, and DABSO in the presence of air (O2) with rhodamine B serving as the photocatalyst. A variety of β-keto sulfones were obtained at high yields by this one-pot operation under aerobic atmosphere. This oxysulfonylation procedure has benefits such as mild reaction conditions, a wide tolerance of functional groups, and simplicity, making it a promising choice for preparing valuable β-keto sulfones. [Display omitted] •Photo reaction of β-keto sulfones from aryldiazo tetrafluoroborate salts has been reported.•DABSO and rhodamine were used for synthesis of β-keto sulfones.•Various β-keto sulfones were obtained in high yield.•No metal catalysts are required in this β-keto sulfone synthesis.