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

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 SO22-. The hydroxymethyl sulfone intermediate generated from the catalytic process can be employed as a synthetic handle to deliver a variety of sulfonyl-containing compounds.

SUBMITTER: Alvarez EM 

PROVIDER: S-EPMC7309323 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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

Alvarez Eva Maria EM   Plutschack Matthew B MB   Berger Florian F   Ritter Tobias T  

Organic letters 20200407 12

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 SO<sub>2</sub><sup>2-</sup>.  ...[more]

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