Synthesis of (Poly)halo‐Substituted Diarylsulfones through Palladium‐Catalyzed C–H Bond Sulfonylation Using (Poly)Halobenzenesulfonyl Chlorides. Issue 44 (23rd August 2018)

• Record Type: Journal Article
• Authors: Sasmal, Arpan; Bera, Jitendra K.; Doucet, Henri; Soulé, Jean‐François
• Other Names: Besset Tatiana guestEditor.; McGlacken Gerard guestEditor.; Schnürch Michael guestEditor.
• Is Part Of: European journal of organic chemistry. Issue 44(2018)
• Page Start: 6114
• Page End: 6120
• Publication Date: 2018-08-23
• Subjects: C–H activation -- Sulfonylation -- Palladium -- Halogenation -- Sulfones; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201800819
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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 Ag2 CO3 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. Abstract : A one‐step procedure for the synthesis of (poly)halo‐substituted diarylsulfones was developed. The reaction involves ortho C–H bond sulfonylation of 2‐arylpyridines with (poly)halo‐substituted benzenesulfonyl chlorides. These reaction conditions tolerated C–F, C–Cl, C–Br and even C–I bonds.