Departamento de Ciencias Químicas, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 954, CP 1113, Buenos Aires, Argentina.
ISOF, Consiglio Nazionale Delle Ricerche, Via P. Gobetti 101, 40129, Bologna, Italy.
Photochem Photobiol Sci. 2021 Aug;20(8):971-983. doi: 10.1007/s43630-021-00078-y. Epub 2021 Jul 20.
The electron-rich nature of aminoaromatic compounds and the electrophilic character of fluoroalkyl R radicals allow for a special match in substitution reactions. We herein present visible light photocatalyzed fluoroalkylation reactions of aniline derivatives, with a study of the reaction mechanisms. The examples evaluated make use of different photocatalysts, such as polypyridyl complexes of Ir or Ru transition metals, organic dyes such as Rose Bengal, phthalocyanine-metal organocatalysts, or visible-light activated complexes. Different visible light sources that span from the blue region of the electromagnetic spectrum to low power red light irradiation sources deliver the excited photocatalysts that ensue into the production of fluoroalkyl R radicals. In turn, many sources of R radicals can be employed, such as fluoroalkyl halides, Togni's reagents, Umemoto's reagent, etc. All these protocol variants demonstrate the expansion of the methodology and the versatility of photocatalytic techniques applied to a special family of organic compounds such as aminoaromatic substrates, which has been studied by different groups. Contributions from our own laboratory will be given.
芳基胺化合物的富电子性质和氟烷基 R 自由基的亲电性使得取代反应能够达到特殊的匹配。我们在此提出可见光光催化的苯胺衍生物的氟烷基化反应，并对反应机理进行了研究。所评估的实例利用了不同的光催化剂，如 Ir 或 Ru 过渡金属的多吡啶配合物、Rose Bengal 等有机染料、酞菁-金属有机催化剂或可见光激活的配合物。不同的可见光源，从电磁光谱的蓝色区域到低功率的红光辐射源，提供了激发态的光催化剂，从而产生氟烷基 R 自由基。反过来，许多 R 自由基的来源都可以被利用，如氟烷基卤化物、Togni 试剂、Umemoto 试剂等。所有这些方案变体都证明了该方法的扩展和光催化技术在如芳基胺底物等特殊有机化合物家族中的应用的多功能性，不同的研究小组已经对其进行了研究。我们实验室的贡献也将被给出。
