ArticleNature communications2017
Regioselective synthesis of C3 alkylated and arylated benzothiophenes.
Article in Nature communications, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- 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
- Asymmetric Synthesis of β-Ketoamides by Sulfonium Rearrangement.Angewandte Chemie (International ed. in English) · 2024Article
- From perfluoroalkyl aryl sulfoxides toBeilstein journal of organic chemistry · 2024Article
- Mechanistic duality of indolyl 1,3-heteroatom transposition.Chemical science · 2023Article
- Metal-Free Arylation of Benzothiophenes at C4 by Activation as their Benzothiophene S-Oxides.Angewandte Chemie (International ed. in English) · 2023Article
- Acyl Azolium-Photoredox-Enabled Synthesis ofACS catalysis · 2023Article
- Synthesis of benzo[RSC advances · 2023Article
- Dearomative di- and trifunctionalization of aryl sulfoxides via [5,5]-rearrangement.Nature communications · 2022Article
- Article
- Modular synthesis of unsymmetrical [1]benzothieno[3,2-Chemical science · 2022Article
- Sulfonium-aided coupling of aromatic rings via sigmatropic rearrangement.Proceedings of the Japan Academy. Series B, Physical and biological sciences · 2022Article
- Interrupted reactions in chemical synthesis.Nature reviews. Chemistry · 2021Review
- Asymmetric systematic synthesis, structures, and (chir)optical properties of a series of dihetero[8]helicenes.Chemical science · 2021Article
- Trifluoromethyl Sulfoxides: Reagents for Metal-Free C-H Trifluoromethylthiolation.Angewandte Chemie (International ed. in English) · 2020Article
- Dearomatization of aryl sulfoxides: a switch between mono- and dual-difluoroalkylation.Chemical science · 2020Article
- Sulfoxide-mediated oxidative cross-coupling of phenols.Chemical science · 2020Article
- Vinyl Cation Stabilization by Silicon Enables a Formal Metal-Free α-Arylation of Alkyl Ketones.Angewandte Chemie (International ed. in English) · 2019Article
- Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.Chemical reviews · 2019Article
- Dual vicinal functionalisation of heterocyclesChemical science · 2018Article
- A bioinspired and biocompatible ortho-sulfiliminyl phenol synthesis.Nature communications · 2017Article
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Benzothiophenes are heterocyclic constituents of important molecules relevant to society, including those with the potential to meet modern medical challenges. The construction of molecules would be vastly more efficient if carbon-hydrogen bonds, found in all organic molecules, can be directly converted into carbon-carbon bonds. In the case of elaborating benzothiophenes, functionalization of carbon-hydrogen bonds at carbon-number 3 (C3) is markedly more demanding than at C2 due to issues of regioselectivity (C3 versus C2), and the requirement of high temperatures, precious metals and the installation of superfluous directing groups. Herein, we demonstrate that synthetically unexplored but readily accessible benzothiophene S-oxides serve as novel precursors for C3-functionalized benzothiophenes. Employing an interrupted Pummerer reaction to capture and then deliver phenol and silane coupling partners, we have discovered a directing group-free method that delivers C3-arylated and -alkylated benzothiophenes with complete regioselectivity, under metal-free and mild conditions.
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Registered trials
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