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Synlett 2014; 25(12): 1731-1734
DOI: 10.1055/s-0033-1341272
letter
© Georg Thieme Verlag Stuttgart · New York

Silver-Mediated Radical Trifluoromethylarylation of Activated Alkenes for the Synthesis of Oxindoles Bearing a CF3 Group

Yao-Feng Wang
Department of Applied Chemistry, School of Chemical Engineering & the Environment, Beijing Institute of Technology, 5 South Zhongguancun Street, Haidian District, Beijing 100081, P. R. of China   Fax: +86(10)68918296   Email: fuxue.chen@bit.edu.cn
,
Jiashen Qiu
Department of Applied Chemistry, School of Chemical Engineering & the Environment, Beijing Institute of Technology, 5 South Zhongguancun Street, Haidian District, Beijing 100081, P. R. of China   Fax: +86(10)68918296   Email: fuxue.chen@bit.edu.cn
,
Dejie Kong
Department of Applied Chemistry, School of Chemical Engineering & the Environment, Beijing Institute of Technology, 5 South Zhongguancun Street, Haidian District, Beijing 100081, P. R. of China   Fax: +86(10)68918296   Email: fuxue.chen@bit.edu.cn
,
Fu-Xue Chen*
Department of Applied Chemistry, School of Chemical Engineering & the Environment, Beijing Institute of Technology, 5 South Zhongguancun Street, Haidian District, Beijing 100081, P. R. of China   Fax: +86(10)68918296   Email: fuxue.chen@bit.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 21 March 2014

Accepted after revision: 28 March 2014

Publication Date:
12 May 2014 (online)

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Abstract

A radical trifluoromethylarylation of N-arylacrylamides with in situ generated [AgCF3] species from Me3SiCF3 and AgF in DMF is established through a tandem radical addition and C–H activation pathway. It provided a concise method to prepare 21 examples of CF3-containing oxindoles within four hours.

Key words

alkenes - xindole - radical reactions - silver - tandem reaction - trifluoromethylation

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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