ArticleACS catalysis2018
Iron(II)-Catalyzed Azidotrifluoromethylation of Olefins and N-Heterocycles for Expedient Vicinal Trifluoromethyl Amine Synthesis.
Article in ACS catalysis, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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16 citing papers in PubMed, 83 citations in OpenAlex.
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- Photochemical diazidation of alkenes enabled by ligand-to-metal charge transfer and radical ligand transfer.Nature communications · 2022Article
- Catalytic Stereoconvergent Synthesis of Homochiral β-CFACS organic & inorganic Au · 2022Article
- Metal-Free Photochemical Imino-Alkylation of Alkenes with Bifunctional Oxime Esters.Journal of the American Chemical Society · 2022Article
- Trifluoromethanesulfonyl azide as a bifunctional reagent for metal-free azidotrifluoromethylation of unactivated alkenes.Chemical science · 2021Article
- Iron-catalyzed domino coupling reactions of π-systems.Beilstein journal of organic chemistry · 2021Review
- Catalytic hydrogen atom transfer to alkenes: a roadmap for metal hydrides and radicals.Chemical science · 2020Review
- Visible-light mediated carbonyl trifluoromethylative amination as a practical method for the synthesis of β-trifluoromethyl tertiary alkylamines.Chemical science · 2020Article
- Iron-catalyzed remote functionalization of inert C(spChemical science · 2020Article
- Revealing the Iron-Catalyzed β-Methyl Scission ofMolecules (Basel, Switzerland) · 2020Article
- Iron-catalyzed carboazidation of alkenes and alkynes.Nature communications · 2019Article
- Enantioselective Synthesis of Oseltamivir Phosphate (Tamiflu) via the Iron-Catalyzed Stereoselective Olefin Diazidation.Journal of the American Chemical Society · 2018Article
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6 authors at 2 institutions in 1 country.
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Abstract
We report herein an iron-catalyzed azidotrifluoromethylation method for expedient vicinal trifluoromethyl primary-amine synthesis. This method is effective for a broad range of olefins and N-heterocycles, and it facilitates efficient synthesis of a wide variety of vicinal trifluoromethyl primary amines, including those that prove difficult to synthesize with existing approaches. Our preliminary mechanistic studies revealed that the catalyst-promoted azido-group transfer proceeds through a carbo-radical instead of a carbocation species. Characterization of an active iron catalyst through X-ray crystallographic studies suggests that in situ generated, structurally novel iron-azide complexes promote the oxidant activation and selective azido-group transfer.
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