Visible-Light-Mediated Trifluoroethylation of N-Arylacrylamides with Trifluoroethyl Iodide: Synthesis of CF3-Containing Oxindoles

Weijun Fu; Mei Zhu; Guanglong Zou; Chen Xu; Zhiqiang Wang

doi:10.1055/s-0034-1379071

Synlett, Table of Contents

Synlett 2014; 25(17): 2513-2517
DOI: 10.1055/s-0034-1379071

letter

Visible-Light-Mediated Trifluoroethylation of N-Arylacrylamides with Trifluoroethyl Iodide: Synthesis of CF₃-Containing Oxindoles

Weijun Fu*

^aCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, P. R. of China Fax: +86(379)669810261 Email: wjfu@lynu.edu.cn

,

Mei Zhu

^aCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, P. R. of China Fax: +86(379)669810261 Email: wjfu@lynu.edu.cn

,

Guanglong Zou

^bSchool of Chemistry and Enviromental Science, Guizhou Minzu Univeristy, Guiyang 550025, P. R. of China Email: scesgzmu@126.com

,

Chen Xu

^aCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, P. R. of China Fax: +86(379)669810261 Email: wjfu@lynu.edu.cn

,

Zhiqiang Wang

^aCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, P. R. of China Fax: +86(379)669810261 Email: wjfu@lynu.edu.cn

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Abstract

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Abstract

A practical and unified strategy has been described for the preparation of CF₃-containing oxindole derivatives using a visible-light-promoted trifluoroethylation reaction of N-arylacrylamides with trifluoroethyl iodide. These reactions could be carried out at room temperature in good to excellent chemical yields with good functional-group tolerance.

Key words

trifluoroethylation - alkenes - oxindole - photoredox - radical reactions

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References

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19 Typical Procedure for Aryltrifluoroethylation of N-Aryl-acrylamides To a mixture of 1a–t (0.3 mmol) CF₃CH₂I (0.9 mmol) and K₂CO₃ (0.6 mmol) in DMF (2.0 mL) was added fac-Ir(ppy)₃ (0.006 mmol, 2.0 mol%) under N₂ atmosphere. The solution was stirred at r.t. under 5 W blue LED irradiation for 24 h. Then the reaction mixture was diluted by adding EtOAc and brine. The aqueous layer was extracted with EtOAc The combined organic layer was dried over MgSO₄, filtered, and concentrated. The residue was purified by flash column chromatography [PE–EtOAc (10:1) as the eluant] on silica gel to give the desired oxindoles.

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