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DABSO as a SO2 Source Usable for Direct Sulfonylative-Suzuki Coupling of Aryl Boronic Acids

Bis(sulfur dioxide)-1,4-diazabicyclo[2.2.2]octane adduct (DABSO) has been widely used as a SO2 source since it was first applied to synthesis of sulfonyl compounds by Willis et al. in 2011.1) For example, Willis et al. have performed the (CH3CN)4CuBF4 complex catalyzed direct sulfonylative-Suzuki coupling of aryl boronic acids with electrophiles using DABSO as a SO2 source. In this reaction, nucleophilic aryl sulfinates are formed as a synthetic intermediate, and further react with various electrophiles like epoxides, in situ prepared chloroamines and an active fluorinating reagent (NFSI) to afford the related sulfones, sulfonamides and sulfonylfluorides.2) DABSO can be used as a SO2 surrogate reagent because gaseous SO2 is highly toxic, so it is expected to be further applied to organic syntheses.

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