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Synlett 2015; 26(01): 45-50
DOI: 10.1055/s-0034-1379497
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© Georg Thieme Verlag Stuttgart · New York

Trifluoromethylation and Pentafluoroethylation of Vinylic Halides with Low-Cost RfH-Derived CuRf (Rf = CF3, C2F5)

Anton Lishchynskyi
Institute of Chemical Research of Catalonia (ICIQ), Avinguda Països Catalans, 16, 43007 Tarragona, Spain   Fax: +34(977)920825   eMail: vgrushin@iciq.es
,
Zahra Mazloomi
Institute of Chemical Research of Catalonia (ICIQ), Avinguda Països Catalans, 16, 43007 Tarragona, Spain   Fax: +34(977)920825   eMail: vgrushin@iciq.es
,
Vladimir V. Grushin*
Institute of Chemical Research of Catalonia (ICIQ), Avinguda Països Catalans, 16, 43007 Tarragona, Spain   Fax: +34(977)920825   eMail: vgrushin@iciq.es
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Publikationsverlauf

Received: 30. September 2014

Accepted: 20. Oktober 2014

Publikationsdatum:
26. November 2014 (online)

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Abstract

A variety of vinylic bromides and iodides undergo smooth trifluoromethylation and pentafluoroethylation with RfH-derived CuRf (Rf = CF3, C2F5) to give the corresponding fluoroalkylated olefins. These reactions employing the low-cost CuRf reagents occur in high yield with excellent chemo- and stereoselectivity under mild conditions (23–80 °C). Crystal structures of one trifluoromethyl and one pentafluoroethyl derivative have been determined.

Key words

trifluoromethylation - pentafluoroethylation - vinylic halides - copper - cross-coupling

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379497.
  • Supporting Information
 

  • References and Notes

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