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Literature DB >> 25102254

Photoredox-induced three-component azido- and aminotrifluoromethylation of alkenes.

Guillaume Dagousset¹, Aude Carboni, Emmanuel Magnier, Géraldine Masson.

Abstract

We report herein a photoredox-catalyzed azidotrifluoromethylation of alkenes. Under the optimized conditions using [Ru(bpy)3(PF6)2] as the photocatalyst and Umemoto's reagent as the CF3 source, a wide range of substituted styrenes as well as various activated and nonactivated alkenes can readily be difunctionalized, affording β-trifluoromethylated azides or amines in good yields.

Entities: Chemical Gene

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Year: 2014 PMID： 25102254 DOI： 10.1021/ol5021477

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

15 in total

1. Iron(II)-Catalyzed Azidotrifluoromethylation of Olefins and N-Heterocycles for Expedient Vicinal Trifluoromethyl Amine Synthesis.

Authors: Cheng-Liang Zhu; Cheng Wang; Qi-Xue Qin; Sam Yruegas; Caleb D Martin; Hao Xu
Journal: ACS Catal Date: 2018-04-20 Impact factor: 13.084

2. Fluorine-decoupled carbon spectroscopy for the determination of configuration at fully substituted, trifluoromethyl- and perfluoroalkyl-bearing carbons: comparison with 19F-1H heteronuclear Overhauser effect spectroscopy.

Authors: Appi Reddy Mandhapati; Takayuki Kato; Takahiko Matsushita; Bashar Ksebati; Andrea Vasella; Erik C Böttger; David Crich
Journal: J Org Chem Date: 2015-01-20 Impact factor: 4.354

3. Three-Component Azidation of Styrene-Type Double Bonds: Light-Switchable Behavior of a Copper Photoredox Catalyst.

Authors: Gabriele Fumagalli; Pauline T G Rabet; Scott Boyd; Michael F Greaney
Journal: Angew Chem Int Ed Engl Date: 2015-06-26 Impact factor: 15.336

4. Redox-Neutral Dual Functionalization of Electron-Deficient Alkenes.

Authors: Fredrik Pettersson; Giulia Bergonzini; Carlo Cassani; Carl-Johan Wallentin
Journal: Chemistry Date: 2017-05-10 Impact factor: 5.236

Review 5. Metal-Catalysed Azidation of Organic Molecules.

Authors: Monalisa Goswami; Bas de Bruin
Journal: European J Org Chem Date: 2016-12-22

6. Metal-free alkene oxy- and amino-perfluoroalkylations via carbocation formation by using perfluoro acid anhydrides: unique reactivity between styrenes and perfluoro diacyl peroxides.

Authors: Elena Valverde; Shintaro Kawamura; Daisuke Sekine; Mikiko Sodeoka
Journal: Chem Sci Date: 2018-08-01 Impact factor: 9.825

Photoredox-induced three-component azido- and aminotrifluoromethylation of alkenes.

1. Iron(II)-Catalyzed Azidotrifluoromethylation of Olefins and N-Heterocycles for Expedient Vicinal Trifluoromethyl Amine Synthesis.

2. Fluorine-decoupled carbon spectroscopy for the determination of configuration at fully substituted, trifluoromethyl- and perfluoroalkyl-bearing carbons: comparison with 19F-1H heteronuclear Overhauser effect spectroscopy.

3. Three-Component Azidation of Styrene-Type Double Bonds: Light-Switchable Behavior of a Copper Photoredox Catalyst.

4. Redox-Neutral Dual Functionalization of Electron-Deficient Alkenes.

Review 5. Metal-Catalysed Azidation of Organic Molecules.

6. Metal-free alkene oxy- and amino-perfluoroalkylations via carbocation formation by using perfluoro acid anhydrides: unique reactivity between styrenes and perfluoro diacyl peroxides.

7. Characterizing Chain Processes in Visible Light Photoredox Catalysis.

8. Redox-ligand sustains controlled generation of CF₃ radicals by well-defined copper complex.

9. Ruthenium-Catalyzed Site-Selective Trifluoromethylations and (Per)Fluoroalkylations of Anilines and Indoles.

10. Synthesis of Functionalized Cyclopropanes from Carboxylic Acids by a Radical Addition-Polar Cyclization Cascade.