Radical Reactivity of Frustrated Lewis Pairs with Diaryl Esters - data

Here we report the reaction of diaryl substituted esters with frustrated Lewis pairs. Interestingly this results in divergent pathways, one whereby the diaryl moiety is stabilized by the Lewis basic phosphine or the alternative pathway, wherein a single-electron transfer process occurs generating the [Mes3P]+·/[C(H)Ar2]· radical ion pair. The latter species undergoes a homocoupling reaction to yield tetraphenylethane derivatives. In the presence of olefins, this reactivity can be harnessed through an sp2-sp3 C–C heterocoupling reaction to generate α,β-substituted olefins. Notably, this work showcases a frustrated Lewis pair approach to metal-free radical C–H bond activation with subsequent C–C bond formation which also displays complementary reactivity to other approaches. Data includes description of experimental procedures, NMR data and X-ray data.Research results based upon these data can be found at https://doi.org/10.1016/j.xcrp.2020.100016

本研究报告了芳基取代酯与受阻路易斯对的反应。有趣的是，这导致了不同的反应路径：一方面，通过路易斯碱性膦或替代路径，芳基部分得到稳定；另一方面，发生单电子转移过程，生成[Mes3P]+·/[C(H)Ar2]·自由基离子对。后者通过同偶联反应生成四苯基乙烷衍生物。在烯烃的存在下，这种反应性可以通过sp2-sp3 C–C杂环偶联反应来利用，从而生成α,β-取代烯烃。值得注意的是，这项研究展示了受阻路易斯对在金属自由基C–H键活化中的应用，随后形成C–C键，同时也表现出与其他方法互补的反应活性。数据包括实验过程描述、核磁共振数据以及X射线数据。基于这些数据的研究成果可在https://doi.org/10.1016/j.xcrp.2020.100016找到。