Despite common occurrence in molecules of value, methods for transforming sulfonamides are distinctly lacking. Here we introduce easy-to-access sulfonyl pyrroles as synthetic linchpins for sulfonamide functionalization. The versatility of the sulfonyl pyrrole unit is shown by generating a variety of products through chemical, electrochemical and photochemical pathways. Preliminary results on the direct functionalization of primary sulfonamides are also provided, which may lead to new modes of activation.
Treatment of 1-aryl-2,5-diphenylpyrroles with lithium powder at ambient temperature in THF results in the generation of the corresponding aryllithium reagents through reductive C-N bond cleavage.
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