Combining photoredox-catalyzed trifluoromethylation and oxidation with DMSO: facile synthesis of α-trifluoromethylated ketones from aromatic alkenes.
Combining photoredox-catalyzed trifluoromethylation and oxidation with DMSO: facile synthesis of α-trifluoromethylated ketones from aromatic alkenes.
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DOI：
10.1002/anie.201403590
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发表时间：
2014-07
影响因子：
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通讯作者：
Ren Tomita;Yusuke Yasu;T. Koike;M. Akita
中科院分区：
文献类型：
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作者：
Ren Tomita;Yusuke Yasu;T. Koike;M. Akita
三氟甲基化酮是具有三氟甲基的有机化合物的有用结构单元。通过芳香族烯烃的一锅光氧化还原催化的三氟甲基化-氧化序列，可以轻松地合成在 α 位具有三氟甲基取代基的酮。在这些光催化条件下，二甲亚砜 (DMSO) 充当关键且温和的氧化剂。此外，事实证明，铱光催化剂 fac[Ir(ppy)3 ]（ppy=2-苯基吡啶）对于当前的光氧化还原过程至关重要。
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.