ArticleAngewandte Chemie (International ed. in English)2023
Metal-Free Arylation of Benzothiophenes at C4 by Activation as their Benzothiophene S-Oxides.
Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Synthesis of Sterically Congested Carbonyl Compounds via anJournal of the American Chemical Society · 2025Article
- Transition Metal-Free Formal C─H/C─H Coupling of Arylacetamides and Sulfoxides: An Interrupted Pummerer/[2,3]-sigmatropic Rearrangement Sequence.Angewandte Chemie (International ed. in English) · 2025Article
- Direct Activation of Sulfides by C-H Oxidation with Photoexcited Nitroarenes: Formal Manipulations of the C─S Bond.Angewandte Chemie (International ed. in English) · 2025Article
- CspChemical science · 2024Review
- Metal-Free Arylation of Benzothiophenes at C4 by Activation as their Benzothiophene S-Oxides.Angewandte Chemie (International ed. in English) · 2023Article
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7 authors.
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Abstract
Benzothiophenes, activated by oxidation to the corresponding S-oxides, undergo C-H/C-H-type coupling with phenols to give C4 arylation products. While an electron-withdrawing group at C3 of the benzothiophene is important, the process operates without a directing group and a metal catalyst, thus rendering it compatible with sensitive functionalities-e.g. halides and formyl groups. Quantum chemical calculations suggest a formal stepwise mechanism involving heterolytic cleavage of an aryloxysulfur species to give a π-complex of the corresponding benzothiophene and a phenoxonium cation. Subsequent addition of the phenoxonium cation to the C4 position of the benzothiophene is favored over the addition to C3; Fukui functions predict that the major regioisomer is formed at the more electron-rich position between C3 and C4. Varied selective manipulation of the benzothiophene products showcase the synthetic utility of the metal-free arylation process.
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