ArticleNature communications2015
Radical cascade reaction of alkynes with N-fluoroarylsulfonimides and alcohols.
Article in Nature communications, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 122 citations in OpenAlex.
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- Mn(I)-catalyzed sigmatropic rearrangement of β, γ-unsaturated alcohols.Nature communications · 2023Article
- Functionalisation of ethereal-based saturated heterocycles with concomitant aerobic C-H activation and C-C bond formation.Chemical science · 2022Article
- Copper-catalyzed radical cascade reaction of simple cyclobutanes: synthesis of highly functionalized cyclobutene derivatives.Chemical science · 2022Article
- NHC and visible light-mediated photoredox co-catalyzed 1,4-sulfonylacylation of 1,3-enynes for tetrasubstituted allenyl ketones.Chemical science · 2022Article
- Ligand-free copper-catalyzed C(spRSC advances · 2021Article
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- Synthesis of difluoromethylated allenes through trifunctionalization of 1,3-enynes.Nature communications · 2020Article
- Mechanistic Aspects and Synthetic Applications of Radical Additions to Allenes.Chemical reviews · 2019Article
- Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes.Angewandte Chemie (International ed. in English) · 2017Article
- Visible light amination/Smiles cascade: access to phthalazine derivatives.Chemical science · 2016Article
- Radical Smiles Rearrangement: An Update.Molecules (Basel, Switzerland) · 2016Review
- Copper-catalyzed aminooxygenation of styrenes with N-fluorobenzenesulfonimide and N-hydroxyphthalimide derivatives.Beilstein journal of organic chemistry · 2015Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Cascade reactions initiated by radical addition to alkynes are synthetically very attractive because they enable access to highly complex molecular skeletons in only few synthetic steps under usually mild conditions. Here we report a general radical cascade reaction of alkynes, N-fluoroarylsulfonimides and alcohols, enabling the efficient synthesis of important α-amino-α-aryl ketones from readily available starting materials via a single operation. During this process, the highly regioselective nitrogen-centred radical addition to internal and terminal alkynes generating vinyl radicals and the next explicit migration of aryl group from the nitrogen source lead the following efficient desulfonylation, oxygenation, and semi-pinacol rearrangement. In addition, the semi-pinacol rearrangement precursors, α-alkyloxyl-α,α-diaryl imines, could also be efficiently obtained under milder conditions. This methodology might open a new entry for designing intermolecular radical cascade reaction of alkynes.
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