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Combining Photoredox‐Catalyzed Trifluoromethylation and Oxidation with DMSO: Facile Synthesis of α‐Trifluoromethylated Ketones from Aromatic Alkenes
Author(s) -
Tomita Ren,
Yasu Yusuke,
Koike Takashi,
Akita Munetaka
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201403590
Subject(s) - trifluoromethylation , chemistry , trifluoromethyl , photoredox catalysis , photocatalysis , substituent , iridium , dimethyl sulfoxide , catalysis , organic chemistry , sulfoxide , photochemistry , combinatorial chemistry , alkyl
Trifluoromethylated ketones are useful building blocks for organic compounds with a trifluoromethyl group. A new and facile synthesis of ketones with a trifluoromethyl substituent in the α‐position proceeds through a one‐pot photoredox‐catalyzed trifluoromethylation–oxidation sequence of aromatic alkenes. Dimethyl sulfoxide (DMSO) serves as a key and mild oxidant under these photocatalytic conditions. Furthermore, an iridium photocatalyst, fac [Ir(ppy) 3 ] (ppy=2‐phenylpyridine), turned out to be crucial for the present photoredox process.