Synthesis of 4-(Bromodifluoromethylseleno) Isocoumarins via Selenolation/Lactonization of 2-Alkynylbenzoates Enabled by a Multi-Component Reagents System.

J Org Chem

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Faculty of Medicine, Tianjin University, Tianjin 300072, China.

Published: January 2025

-CFBnSeCFBr was developed as a bromodifluoromethylselenonating reagent, which was utilized by combining with CPBA and TfO for the synthesis of 4-(bromodifluoromethylseleno) isocoumarins via the selenolation/lactonization of 2-alkynylbenzoates. The transformation was postulated to proceed via a multicomponent reagents system-enabled sequence involving the oxidation of -CFBnSeCFBr by CPBA into its selenium sulfoxide, activation of the generated sulfoxide by TfO into the electrophilic -CFBnSeOCFBr salt, and selenolation/lactonization of 2-alkynylbenzoates by the reactive electrophilic species into 4-(bromodifluoromethylseleno) isocoumarins.

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http://dx.doi.org/10.1021/acs.joc.4c02696DOI Listing

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Synthesis of 4-(Bromodifluoromethylseleno) Isocoumarins via Selenolation/Lactonization of 2-Alkynylbenzoates Enabled by a Multi-Component Reagents System.

J Org Chem

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Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Faculty of Medicine, Tianjin University, Tianjin 300072, China.

-CFBnSeCFBr was developed as a bromodifluoromethylselenonating reagent, which was utilized by combining with CPBA and TfO for the synthesis of 4-(bromodifluoromethylseleno) isocoumarins via the selenolation/lactonization of 2-alkynylbenzoates. The transformation was postulated to proceed via a multicomponent reagents system-enabled sequence involving the oxidation of -CFBnSeCFBr by CPBA into its selenium sulfoxide, activation of the generated sulfoxide by TfO into the electrophilic -CFBnSeOCFBr salt, and selenolation/lactonization of 2-alkynylbenzoates by the reactive electrophilic species into 4-(bromodifluoromethylseleno) isocoumarins.

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