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Cross-coupling of sulfonic acid derivatives via aryl-radical transfer (ART) using TTMSS or photoredox

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Abstract

The intramolecular cross-coupling of sulfonic acid derivatives occurs in the presence of tris(trimethylsilyl)silane (TTMSS) at room temperature and in air to form biaryl compounds. A photoredox-catalyzed procedure is also described. These protocols provide mild and convenient alternatives to standard tin-mediated reactions. Combined with the trivial preparation of the substrates from activated sulfonic acids and 2-halophenols or anilines, this work presents a useful means to employ sulfonic acid derivatives in cross-coupling transformations. A modified linker to realize high regioselectivity is also presented. Finally, a one-pot cross-coupling procedure is demonstrated.

Graphical abstract: Cross-coupling of sulfonic acid derivatives via aryl-radical transfer (ART) using TTMSS or photoredox

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Publication details

The article was received on 16 Aug 2017, accepted on 14 Sep 2017 and first published on 20 Sep 2017


Article type: Research Article
DOI: 10.1039/C7QO00731K
Citation: Org. Chem. Front., 2018, Advance Article
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    Cross-coupling of sulfonic acid derivatives via aryl-radical transfer (ART) using TTMSS or photoredox

    E. D. Nacsa and T. H. Lambert, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00731K

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