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Synthesis of (Poly)halo‐Substituted Diarylsulfones through Palladium‐Catalyzed C–H Bond Sulfonylation Using (Poly)Halobenzenesulfonyl Chlorides
Author(s) -
Sasmal Arpan,
Bera Jitendra K.,
Doucet Henri,
Soulé JeanFrançois
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800819
Subject(s) - palladium , chemistry , halo , catalysis , cleavage (geology) , medicinal chemistry , bond cleavage , reactivity (psychology) , polymer chemistry , organic chemistry , materials science , physics , medicine , alternative medicine , pathology , quantum mechanics , galaxy , fracture (geology) , composite material
The reactivity of (poly)halo‐substituted benzenesulfonyl chlorides in palladium‐catalyzed ortho ‐directed C–H bond sulfonylation of 2‐arylpyridines was investigated. The use of Ag 2 CO 3 in concert with Cu(OAc) 2 was found to be critical to promote the chemoselective sulfonylation reaction. Fluoro‐, chloro‐, bromo‐, and even iodo‐benzenesulfonyl chlorides react nicely to afford halo‐substituted diarylsulfones in good to high yields without cleavage of the C–halo bonds, allowing further transformations.