Site-Selective C–H Functionalization–Sulfination Sequence to Access Aryl 
Sulfonamides

Alvarez, Eva Maria; Plutschack, Matthew B.; Berger, Florian; Ritter, Tobias

doi:10.1021/acs.orglett.0c00982

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Site-Selective C–H Functionalization–Sulfination Sequence to Access Aryl Sulfonamides

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Alvarez, Eva Maria
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Plutschack, Matthew B.
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Berger, Florian
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Ritter, Tobias
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Alvarez, E. M., Plutschack, M. B., Berger, F., & Ritter, T. (2020). Site-Selective C–H Functionalization–Sulfination Sequence to Access Aryl Sulfonamides. Organic Letters, 22(12), 4593-4596. doi:10.1021/acs.orglett.0c00982.

Cite as: https://hdl.handle.net/21.11116/0000-0006-98F0-F

Abstract

Aryl sulfinates are precursors to a diverse number of sulfonyl-derived arenes, which are common motifs in pharmaceuticals and agrochemicals. Here, we report a site-selective two-step C–H sulfination sequence via aryl sulfonium salts to access aryl sulfonamides. Combined with site-selective aromatic thianthrenation, an operationally simple one-pot palladium-catalyzed protocol introduces the sulfonyl group using sodium hydroxymethylsulfinate (Rongalite) as a source of SO₂^2–. The hydroxymethyl sulfone intermediate generated from the catalytic process can be employed as a synthetic handle to deliver a variety of sulfonyl-containing compounds.