A hexafluoroisopropanol
(HFIP)-promoted hydroxydifluoromethylation
of aniline, indole, and pyrrole derivatives with difluoroacetaldehyde
ethyl hemiacetal has been developed. This protocol provides a facile
and straightforward approach to access diverse difluoromethylated
carbinols in good to excellent yields under mild conditions. Furthermore,
gram-scale and synthetic derivatization experiments have also been
demonstrated.
A multicomponent dearomative difluoroalkylation of isoquinolines has been developed with difluorinated silyl enol ethers serving as poor nucleophiles without an additional transition-metal or organic catalyst. The sequential oxidative rearomatization under different alkaline conditions provides a controllable formal C−H difluoroalkylation and difluoromethylation method for isoquinolines without peroxide or metal oxidant. A series of isoquinolines including a pharmaceutical, phenanthridine, quinolines, and difluorinated silyl enol ethers were suitable substrates to construct gem-difluorinated heterocycles. The inexpensive starting materials, mild reaction conditions, and simple operation also show practical and environmentally benign advantages.
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