Photocatalytic redox-neutral selective single C(sp3)-F bond activation of perfluoroalkyl iminosulfides with alkenes and water

Visible-light-promoted site-selective and direct C-F bond functionalization of polyfluorinated iminosulfides was accomplished with alkenes and water under redox-neutral conditions, affording a diverse array of gamma-lactams with a fluoro- and perfluoroalkyl-substituted carbon centre. A variety of perfluoroalkyl units, including C2F5, C3F7, C4F9, and C5F11 underwent site-selective defluorofunctionalization. This protocol allows high chemoselectivity control and shows excellent functional group tolerance. Mechanistic studies reveal that the remarkable changes of the electron geometries during the defluorination widen the redox window between the substrates and the products and ensure the chemoselectivity of single C(sp(3))-F bond cleavage.

Automated summary

Visible-light-promoted site-selective and direct C-F bond functionalization of polyfluorinated iminosulfides allows the synthesis of gamma-lactams with a fluoro- and perfluoroalkyl-substituted carbon centre. The reaction shows high chemoselectivity control and excellent functional group tolerance.