Visible-Light-Induced Selective Photolysis of Phosphonium Iodide Salts for Monofluoromethylations
Visible-Light-Induced Selective Photolysis of Phosphonium Iodide Salts for Monofluoromethylations
复制标题
可见光诱导碘化鏻盐选择性光解单氟甲基化
DOI：
10.1002/anie.202111006
复制
发表时间：
2021-10-22
影响因子：
16.6
通讯作者：
Chen, Xiang-Yu
中科院分区：
文献类型：
--
作者：
Liu, Qiang;Lu, Yu;Chen, Xiang-Yu
西格玛(Sigma)-空穴效应已成为构造具有新性质的新型结构的一种很有前途的工具。一种简单而有效的产生单氟甲基自由基的策略在合成社区内是一个持续的挑战。氟甲基膦盐很容易获得，对空气和热稳定性都很稳定，而且操作简单。在这里，我们报道了Sigma-Hole效应能够促进可见光触发的碘化膦盐的光解，这是一种电荷转移络合物，选择性地产生氟甲基自由基。通过多种烯烃的单氟甲基化、双氟甲基化和三氟甲基化反应，证明了这一新方案的实用性和通用性。
The sigma (sigma)-hole effect has emerged as a promising tool to construct novel architectures endowed with new properties. A simple yet effective strategy for the generation of monofluoromethyl radicals is a continuing challenge within the synthetic community. Fluoromethylphosphonium salts are easily available, air- and thermally stable, as well as simple-to-handle. Herein, we report the ability of the sigma-hole effect to facilitate the visible-light-triggered photolysis of phosphonium iodide salts, a charge-transfer complex, selectively giving fluoromethyl radicals. The usefulness and versatility of this new protocol are demonstrated through the mono-, di-, and trifluoromethylation of a variety of alkenes.