4.3 Article

Flash generation and borylation of 1-(trifluoromethyl)vinyllithium toward synthesis of alpha-(trifluoromethyl)styrenes

Journal

JOURNAL OF FLUORINE CHEMISTRY
Volume 207, Issue -, Pages 72-76

Publisher

ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2018.01.004

Keywords

Flow microreactor; (Trifluoromethyl)vinyl compounds; Lithiation; Borylation; Suzuki-Miyaura coupling; Palladium catalyst

Funding

  1. JSPS KAKENHI [JP16H04105, JP16H01002, JP16K20939]
  2. Grants-in-Aid for Scientific Research [16H04105, 16H01002, 17J05462] Funding Source: KAKEN

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Thermally unstable (3,3,3-trifluoroprop-1-en-2-yl)lithium was generated by lithiation of 2-bromo-3,3,3-tri-fluoroprop-1-ene and successively underwent borylation in a flow microreactor system. Direct use of the 1-(trifluoromethyl)vinylborate thus formed for the Suzuki-Miyaura coupling in a batch system afforded alpha-(tri-fluoromethyl)styrenes in high yields.

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