Primary Sulfonamide Functionalization via Sulfonyl Pyrroles: Seeing the N−Ts Bond in a Different Light

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...

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Bibliographic Details
Published in:Chemistry : a European journal 2021-11, Vol.27 (62), p.15387-15391
Main Authors: Ozaki, Tomoya, Yorimitsu, Hideki, Perry, Gregory J. P.
Format: Article
Language:English
Subjects:
deprotection
electrochemistry
late-stage functionalization
photoredox
sulfonamide
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Summary: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. Sulfonamides are prevalent in drug molecules, however, methods for functionalizing sulfonamides via S−N bond cleavage are scarce. Based on a re‐evaluation of N−Ts deprotection, we developed sulfonyl pyrroles as linchpins for sulfonamide functionalization. Sulfonyl pyrroles engage in various transformations that can proceed through chemical, electrochemical or photochemical pathways.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202102748