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Aromatic Chlorosulfonylation by Photoredox Catalysis
Author(s) -
Májek Michal,
Neumeier Michael,
Jacobi von Wangelin Axel
Publication year - 2017
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201601293
Subject(s) - photoredox catalysis , chemistry , catalysis , halide , acetonitrile , photocatalysis , aqueous solution , photochemistry , nitro , visible spectrum , combinatorial chemistry , organic chemistry , alkyl , materials science , optoelectronics
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 SO 2 and HCl (from aqueous SOCl 2 ). 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, CF 3 , SF 5 , esters, heteroarenes). Theoretical and experimental studies support a photoredox‐catalysis mechanism.