Fluorinated Sulfilimino Iminiums: Efficient and Versatile Sources of Perfluoroalkyl Radicals under Photoredox Catalysis.

Authors :: Daniel M
Dagousset G
Diter P
Klein PA
Tuccio B
Goncalves AM
Masson G
Magnier E
Source :: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2017 Mar 27; Vol. 56 (14), pp. 3997-4001. Date of Electronic Publication: 2017 Mar 02.
Publication Year :: 2017
Abstract: Reported herein is the use of S-perfluoroalkyl sulfilimino iminiums as a new source of R <subscript>F</subscript> radicals under visible-light photoredox catalysis (R <subscript>F</subscript> =CF <subscript>3</subscript> , C <subscript>4</subscript> F <subscript>9</subscript> , CF <subscript>2</subscript> Br, CFCl <subscript>2</subscript> ). These shelf-stable perfluoroalkyl reagents, readily prepared on gram scale from the corresponding sulfoxide using a one-pot procedure, allow the efficient photoredox-induced oxyperfluoroalkylation of various alkenes using fac-Ir(ppy) <subscript>3</subscript> as the photocatalyst. Importantly, spin-trapping/electron paramagnetic resonance experiments were carried out to characterize all the radical intermediates involved in this radical/cationic process.<br /> (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

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