Synthesis of (Poly)halo-substituted Diarylsulfones through Palladium Catalyzed C-H Bond Sulfonylation using (Poly)Halobenzenesulfonyl Chlorides

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 Ag2CO3 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.
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Arpan Sasmal, Jitendra K. Bera, Henri Doucet, Jean-François Soulé. Synthesis of (Poly)halo-substituted Diarylsulfones through Palladium Catalyzed C-H Bond Sulfonylation using (Poly)Halobenzenesulfonyl Chlorides. European Journal of Organic Chemistry, Wiley-VCH Verlag, In press, 2018 (44), pp.6114-6120. ⟨10.1002/ejoc.201800819⟩. ⟨hal-01915420⟩

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