Forging C‐SeCF 3 Bonds with Trifluoromethyl Tolueneselenosulfonate under Visible‐Light

Dan Louvel , Clément Ghiazza , Vincent Debrauwer , Lhoussain Khrouz , Cyrille Monnereau , Anis Tlili (1)

1 CNRS - Centre National de la Recherche Scientifique

This account highlights some of our recent work on photoinduced trifluoromethylselenolation reactions. This research program relies primarily on the design of a new key shelf-stable selenating reagent that can be involved in various radical processes In particular, we demonstrated that trifluoromethylselenolation of arenes, alkenes, alkynes as well as aliphatic organic building blocks can be readily achieved under visible-light irradiation. Mechanistic investigations based on 19 F NMR studies, EPR spectroscopy, cyclic voltammetry and luminescence studies allowed us to shed the light on the different proposed mechanisms in the designed methodologies. The applicative potential of these strategies was further demonstrated through the synthesis of bioactive analogue containing SeCF3 motif.

Domaines: Chimie

Dan Louvel, Clément Ghiazza, Vincent Debrauwer, Lhoussain Khrouz, Cyrille Monnereau, et al.. Forging C‐SeCF 3 Bonds with Trifluoromethyl Tolueneselenosulfonate under Visible‐Light. Chemical Record, 2021, 21 (2), pp.417-426. ⟨10.1002/tcr.202000184⟩. ⟨hal-03394540⟩