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Synlett 2014; 25(17): 2513-2517
DOI: 10.1055/s-0034-1379071
DOI: 10.1055/s-0034-1379071
letter
Visible-Light-Mediated Trifluoroethylation of N-Arylacrylamides with Trifluoroethyl Iodide: Synthesis of CF3-Containing Oxindoles
Further Information
Publication History
Received: 12 June 2014
Accepted after revision: 11 July 2014
Publication Date:
18 August 2014 (online)
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.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- Supporting Information
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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.
For recent reviews, see:
For recent reviews on visible-light-induced photocatalysis, see: