ArticleChemical science2017
CuH-catalysed hydroamination of arylalkynes with hydroxylamine esters - a computational scrutiny of rival mechanistic pathways.
Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Anti-Markovnikov Intermolecular Hydroamination of Alkenes and Alkynes: A Mechanistic View.Chemical reviews · 2023Review
- Article
- An umpolung-enabled copper-catalysed regioselective hydroamination approach to α-amino acids.Chemical science · 2021Article
- Diastereo- and Enantioselective CuH-Catalyzed Hydroamination of Strained Trisubstituted Alkenes.ACS catalysis · 2020Article
- Regio- and Enantioselective Synthesis of 1,2-Diamine Derivatives by Copper-Catalyzed Hydroamination.Organic letters · 2019Article
- Mechanistically Guided Design of Ligands That Significantly Improve the Efficiency of CuH-Catalyzed Hydroamination Reactions.Journal of the American Chemical Society · 2018Article
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Authors and funding
1 author.
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Abstract
An in-depth computational mechanistic probe of the CuH-mediated hydroamination of internal arylalkynes with an archetype hydroxylamine ester and hydrosilane by a (Xantphos)CuH catalyst (Xantphos ≡ {P^P} ≡ 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene) is presented. This first comprehensive computational study of the CuH-mediated electrophilic alkyne hydroamination has identified the most accessible pathway for the rival avenues for direct and reductive hydroamination. The mechanistic picture derived from smooth energy profiles obtained by employing a reliable computational protocol applied to a realistic catalyst model conforms to all available experimental data. The crucial vinyl- and alkylcopper intermediates were found to display a distinct chemodivergence in their reactivity towards amine electrophile and alcohol, which ensures the successful formation of α-branched alkylamines together with (
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