3360-56-3Relevant articles and documents
Photoinduced Trifluoromethylation of Arenes and Heteroarenes Catalyzed by High-Valent Nickel Complexes
Deolka, Shubham,Govindarajan, Ramadoss,Khaskin, Eugene,Fayzullin, Robert R.,Roy, Michael C.,Khusnutdinova, Julia R.
supporting information, p. 24620 - 24629 (2021/10/08)
We describe a series of air-stable NiIII complexes supported by a simple, robust naphthyridine-based ligand. Access to the high-valent oxidation state is enabled by the CF3 ligands on the nickel, while the naphthyridine exhibits either a monodentate or bidentate coordination mode that depends on the oxidation state and sterics, and enables facile aerobic oxidation of NiII to NiIII. These NiIII complexes act as efficient catalysts for photoinduced C(sp2)?H bond trifluoromethylation reactions of (hetero)arenes using versatile synthetic protocols. This blue LED light-mediated catalytic protocol proceeds via a radical pathway and demonstrates potential in the late-stage functionalization of drug analogs.
Alternating current electrolysis for organic electrosynthesis: Trifluoromethylation of (hetero)arenes
Rodrigo, Sachini,Um, Chanchamnan,Mixdorf, Jason C.,Gunasekera, Disni,Nguyen, Hien M.,Luo, Long
supporting information, p. 6719 - 6723 (2020/07/30)
Paired electrolysis has a limited reaction scope for organic synthesis because it is often not compatible with reactions involving short-lived intermediates. We addressed this limitation using alternating current electrolysis (ACE). Using trifluoromethyla
Electrophotocatalytic Undirected C?H Trifluoromethylations of (Het)Arenes
Qiu, Youai,Scheremetjew, Alexej,Finger, Lars H.,Ackermann, Lutz
supporting information, p. 3241 - 3246 (2020/02/27)
Electrophotochemistry has enabled arene C?H trifluoromethylation with the Langlois reagent CF3SO2Na under mild reaction conditions. The merger of electrosynthesis and photoredox catalysis provided a chemical oxidant-free approach for the generation of the CF3 radical. The electrophotochemistry was carried out in an operationally simple manner, setting the stage for challenging C?H trifluoromethylations of unactivated arenes and heteroarenes. The robust nature of the electrophotochemical manifold was reflected by a wide scope, including electron-rich and electron-deficient benzenes, as well as naturally occurring heteroarenes. Electrophotochemical C?H trifluoromethylation was further achieved in flow with a modular electro-flow-cell equipped with an in-operando monitoring unit for on-line flow-NMR spectroscopy, providing support for the single electron transfer processes.
