College of Chemistry and Molecular Sciences, the Institute for Advanced Studies (IAS), Wuhan University, Wuhan, Hubei, 430072, China.
Nat Commun. 2019 Jan 28;10(1):467. doi: 10.1038/s41467-019-08413-9.
Considering the synthetic value of introducing active alcoholic hydroxyl group, developing C-H functionalization of alcohols is of significance. Herein, we present a photochemical method that under visible light irradiation, selectfluor can effectively promote the oxidative cross-coupling between alcohols and heteroarenes without the external photocatalysis, achieving the selective α sp C-H arylation of alcohol, even in the presence of ether. The N-F activation of selectfluor under blue LEDs irradiation is evidenced by electron paramagnetic resonance (EPR) study, which is the key process for the oxidative activation of α sp C-H alcohols. The observed reactivity may have significant implications for chemical transformations.
考虑到引入活性醇羟基的合成价值，发展醇的 C-H 官能团化具有重要意义。在此，我们提出了一种光化学方法，即在可见光照射下，Selectfluor 可以在没有外加光催化剂的情况下有效促进醇与杂芳烃之间的氧化交叉偶联，实现醇的选择性α sp C-H 芳基化，即使存在醚。通过电子顺磁共振（EPR）研究证实了 Selectfluor 在蓝紫光照射下的 N-F 活化，这是α sp C-H 醇氧化活化的关键过程。所观察到的反应性可能对化学转化具有重要意义。
