Regio- and Stereoselective Synthesis of CF <sub>3</sub> -Containing 1,2- and 1,1-Diarylethenes. Switchable Reaction of β-Halo-β-(trifluoromethyl)styrenes with Boronic Acids
Reaction of β-halo-β-(trifluoromethyl)styrenes with arylboronic acids can be directed in a different way depending on strength of the applied base and order of the reactant mixing. The standard Suzuki cross-coupling (Pd(OAc)<sub>2</sub>/SPhos or Pd(PPh<sub>3</sub>)<sub>4</sub>) using K<sub>3</sub>PO<sub>4</sub> or Na<sub>2</sub>CO<sub>3</sub> as the bases afforded regio- and stereoselectively CF<sub>3</sub>-containing 1,2-diarylethenes (CF<sub>3</sub>-stilbenes) in up to 98% yield. However, pretreatment of these β-halo-β-(trifluoromethyl)styrenes with <i>t</i>-BuOK resulted in formation in situ of the corresponding CF<sub>3</sub>-acetylenes. Subsequent Pd-catalyzed <i>syn</i>-addition of arylboronic acids can be performed as one-pot protocol to open access to CF<sub>3</sub>-containing 1,1-diarylethenes having <i>cis</i>-arranged CF<sub>3</sub> group and aryl moiety of starting styrene. These alkenes were isolated in up to 96% yield. Both types of alkenes can be efficiently reduced into the corresponding CF<sub>3</sub>-substituted ethanes using ammonium formate-Pd/C system.
Authors
- Zoia A. Sizova
- V. G. V. G.
- Vasiliy M. Muzalevskiy
- Andrei A. Vasil’ev
Institutions
- Lomonosov Moscow State University (RU)
- N.D. Zelinsky Institute of Organic Chemistry (RU)
- Moscow State University (TJ)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-01-26
- DOI
- https://doi.org/10.1021/acs.joc.5c02697
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00