title: Aromatic Chlorosulfonylation by Photoredox Catalysis.
abstract: Visible-light photoredox catalysis enables the efficient synthesis of arenesulfonyl chlorides from anilines. The new protocol involves the convenient in situ preparation of arenediazonium salts (from anilines) and the reactive gases SO2and HCl (from aqueous SOCl2). The photocatalytic chlorosulfonylation operates at mild conditions (room temperature, acetonitrile/water) with low catalyst loading. Various functional groups are tolerated (e.g., halides, azides, nitro groups, CF3, SF5, esters, heteroarenes). Theoretical and experimental studies support a photoredox-catalysis mechanism.
authors.affiliation: Institute of Organic Chemistry, University of Regensburg, Universitätsstr. 31, 93040, Regensburg, Germany.
authors.forename: Michal
authors.initials: M
authors.lastname: Májek
authors.affiliation: Institute of Organic Chemistry, University of Regensburg, Universitätsstr. 31, 93040, Regensburg, Germany.
authors.forename: Michael
authors.initials: M
authors.lastname: Neumeier
authors.affiliation: Institute of Organic Chemistry, University of Regensburg, Universitätsstr. 31, 93040, Regensburg, Germany.
authors.forename: Axel
authors.identifier: http://orcid.org/0000-0001-7462-0745
authors.initials: A
authors.lastname: Jacobi von Wangelin
mesh_terms: D000097:Acetonitriles / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D002384:Catalysis; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D013441:Sulfinic Acids / Q000737:chemistry*; D013696:Temperature; D014867:Water / Q000737:chemistry
chemical_list: D000097:Acetonitriles; D000814:Aniline Compounds; D013441:Sulfinic Acids; D014867:Water; C044255:sulfonyl chloride; C032159:acetonitrile
keywords: aromatic substitution; photochemistry; photoredox catalysis; ruthenium; sulfonylation