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Copper-Catalyzed Deoxygenative C2-Sulfonylation of Quinoline N-Oxides with DABSO and Phenyldiazonium Tetrafluoroborates for the Synthesis of 2-Sulfonylquinolines via a Radical Reaction

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An efficient and practical method for the synthesis of 2-sulfonylquinolines through copper-catalyzed deoxygenative C2-sulfonylation of quinoline N-oxides with 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) and phenyldiazonium tetrafluoroborates is demonstrated. Products with various… Click to show full abstract

An efficient and practical method for the synthesis of 2-sulfonylquinolines through copper-catalyzed deoxygenative C2-sulfonylation of quinoline N-oxides with 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) and phenyldiazonium tetrafluoroborates is demonstrated. Products with various substituents were obtained in moderate to high yields.

Keywords: quinoline oxides; deoxygenative sulfonylation; sulfonylation quinoline; catalyzed deoxygenative; copper catalyzed; synthesis sulfonylquinolines

Journal Title: Synthesis
Year Published: 2019

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