Combining Photoredox‐Catalyzed Trifluoromethylation and Oxidation with DMSO: Facile Synthesis of α‐Trifluoromethylated Ketones from Aromatic Alkenes | Zendy

Tomita Ren | Zendy; Yasu Yusuke | Zendy; Koike Takashi | Zendy; Akita Munetaka | Zendy

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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.

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