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Literature DB >> 26088360

Copper-Catalyzed Trifluoromethylazidation of Alkynes: Efficient Access to CF3-Substituted Azirines and Aziridines.

Fei Wang¹, Na Zhu^1,2, Pinhong Chen¹, Jinxing Ye², Guosheng Liu³.

Abstract

A novel method for convenient access to CF3-containing azirines has been developed, and involves a copper-catalyzed trifluoromethylazidation of alkynes and a photocatalyzed rearrangement. Both terminal and internal alkynes are compatible with the mild reaction conditions, thus delivering the CF3-containing azirines in moderate to good yields. The azirines can be converted into various CF3-substituted aziridines.

Entities: Chemical

Keywords: alkynes; copper; heterocycles; rearrangements; synthetic methods

Mesh：

Substances：

Year: 2015 PMID： 26088360 DOI： 10.1002/anie.201503412

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

9 in total

1. Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes.

Authors: Yongquan Ning; Qinghe Ji; Peiqiu Liao; Edward A Anderson; Xihe Bi
Journal: Angew Chem Int Ed Engl Date: 2017-07-07 Impact factor: 15.336

Review 2. Metal-Catalysed Azidation of Organic Molecules.

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

3. Telescoped, Divergent, Chemoselective C1 and C1-C1 Homologation of Imine Surrogates: Access to Quaternary Chloro- and Halomethyl-Trifluoromethyl Aziridines.

Authors: Laura Ielo; Saad Touqeer; Alexander Roller; Thierry Langer; Wolfgang Holzer; Vittorio Pace
Journal: Angew Chem Int Ed Engl Date: 2019-01-24 Impact factor: 15.336

Copper-Catalyzed Trifluoromethylazidation of Alkynes: Efficient Access to CF3-Substituted Azirines and Aziridines.

1. Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes.

Review 2. Metal-Catalysed Azidation of Organic Molecules.

3. Telescoped, Divergent, Chemoselective C1 and C1-C1 Homologation of Imine Surrogates: Access to Quaternary Chloro- and Halomethyl-Trifluoromethyl Aziridines.

4. Iron-catalyzed carboazidation of alkenes and alkynes.

5. Copper-Catalyzed Annulation-Cyanotrifluoromethylation of 1,6-Enynes Toward 1-Indanones via a Radical Process.

6. Asymmetric synthesis of CF₂-functionalized aziridines by combined strong Brønsted acid catalysis.

7. Rhodium-Catalyzed Geminal Oxyfluorination and Oxytrifluoro-Methylation of Diazocarbonyl Compounds.

8. syn-Selective alkylarylation of terminal alkynes via the combination of photoredox and nickel catalysis.

Review 9. Iron-catalyzed domino coupling reactions of π-systems.