Adrien Joliton

Ir-catalyzed preparation of SF5-substituted potassium aryl trifluoroborates via C-H borylation and their application in the Suzuki-Miyaura reaction.

The preparation of new pentafluorosulfanyl-substituted potassium aryltrifluoroborates via Ir-catalyzed C-H borylation is reported. The utility of these novel building blocks was demonstrated in the Suzuki-Miyaura cross-coupling reaction, giving access to 3,5-disubstituted pentafluorosulfanylbenzenes.

Formation of α-SF5-Enolate Enables Preparation of 3-SF5-Quinolin-2-ones, 3-SF5-Quinolines, and 3-SF5-Pyridin-2-ones: Evaluation of their Physicochemical Properties

This study describes, for the first time, the generation of a SF5 -substituted ester enolate from benzyl SF5 -acetate under soft enolization conditions, which in turn participates in aldol addition reactions in high yield. The reaction was applied in the synthesis of 3-SF5 -quinolin-2-ones, 3-SF5 -quinolines, and 3-SF5 -pyridin-2-ones, none of which have previously been reported. To provide guidelines for their use in drug discovery, the physicochemical properties of these building blocks were determined and compared with those of their CF3 - and t-Bu-analogues.