Honeker Roman, Garza-Sanchez R Aleyda, Hopkinson Matthew N, Glorius Frank
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany.
Chemistry. 2016 Mar 18;22(13):4395-9. doi: 10.1002/chem.201600190. Epub 2016 Feb 16.
Herein, we report a new visible-light-promoted strategy to access radical trifluoromethylthiolation reactions by combining halide and photoredox catalysis. This approach allows for the synthesis of vinyl-SCF3 compounds of relevance in pharmaceutical chemistry directly from alkenes under mild conditions with irradiation from household light sources. Furthermore, alkyl-SCF3-containing cyclic ketone and oxindole derivatives can be accessed by radical-polar crossover semi-pinacol and cyclization processes. Inexpensive halide salts play a crucial role in activating the trifluoromethylthiolating reagent towards photoredox catalysis and aid the formation of the SCF3 radical.
在此，我们报道了一种新的可见光促进策略，通过结合卤化物和光氧化还原催化来实现自由基三氟甲硫基化反应。这种方法能够在温和条件下，利用家用光源照射，直接从烯烃合成在药物化学中具有重要意义的乙烯基-SCF3化合物。此外，含烷基-SCF3的环酮和羟吲哚衍生物可通过自由基-极性交叉半频哪醇和环化过程制得。廉价的卤化物盐在激活三氟甲硫基化试剂以进行光氧化还原催化以及促进SCF3自由基的形成方面起着关键作用。
