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Photoredox‐Catalyzed Selective Synthesis of Allylic Perfluoroalkanes from Alkenes
Author(s) -
Barthelemy AnneLaure,
Bourdreux F.,
Dagousset Guillaume,
Magnier Emmanuel
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202002046
Subject(s) - allylic rearrangement , iminium , chemistry , radical , catalysis , trifluoromethyl , selectivity , styrene , combinatorial chemistry , organic chemistry , photochemistry , copolymer , alkyl , polymer
We report herein a novel photoredox‐catalyzed synthesis of allylic trifluoromethanes. The use of sulfilimino iminium as a source of trifluoromethyl radicals proves crucial to achieving high selectivity. Importantly, both styrene derivatives and unactivated alkenes are for the first time suitable partners for this process. The mild reaction conditions are compatible with a variety of functional groups. Remarkably, this method is readily broadened to other perfluoroalkyl groups (R F =CFCl 2 , CF 2 Br, C 4 F 9 ). An extensive mechanistic study is also provided.