Novel Nickel-Catalyzed Synthesis of (Trifluoromethyl)quinolines
T. Kurahashi and S. Matsubara show a new synthetic route to (trifluoromethyl)quinolines.
A New Synthetic Route to (Trifluoromethyl)quinolines: Nickel-Catalyzed Insertion of an Alkyne into an Aromatic C–S Bond by Formation of a Thianickelacycle and Thermal Desulfidation: T. Inami, T. Kurahashi, S. Matsubara
Synlett 2021, 32, DOI: 10.1055/s-0037-1610785
The quinoline scaffold is frequently encountered in natural and bioactive compounds. Incorporation of a trifluoromethyl group on the quinoline ring can impart distinctive biological and pharmaceutical properties, as demonstrated in the case of the antiprotozoal agent mefloquine, which features two trifluoromethyl groups in positions 2 and 8 of the quinoline ring and constitutes one of the most important drugs currently used in the treatment of malaria. For this reason, the development of new methods for preparing trifluoromethyl-substituted quinolines continues to represent an important goal in synthetic organic chemistry. The group of Professors Takuya Kurahashi and Seijiro Matsubara at Kyoto University (Japan) recently reported an original new methodology to access the title compounds, relying on a nickel-catalyzed insertion of an alkyne into the C–S bond of 2-trifluoromethyl-1,3-benzothiazole.
Professor Kurahashi said: “We have succeeded in synthesizing quinolines by a new intermolecular cycloaddition reaction using desulfurization.”