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

Takuya Kurahashi, Seijiro Matsubara, Tasuku Inami
2021 Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry  
AbstractWe have developed a nickel-catalyzed insertion reaction of an alkyne into a 2-(trifluoromethyl)-1,3-benzothiazole to give a seven-membered benzothiazepine that is converted into a 2-(trifluoromethyl)quinoline by thermal desulfidation. This process can be considered a formal substitution of a sulfur atom with an alkyne. The structure of the thianickelacycle intermediate formed through oxidative addition of a C–S bond in the benzothiazole to nickel(0) was confirmed by X-ray single-crystal
more » ... structure analysis and in situ X-ray absorption fine-structure spectroscopy.
doi:10.1055/s-0037-1610785 fatcat:6m2upkujmrf6zcgvnclas5zpxa