Fluoroalkylation of Various Nucleophiles with Fluoroalkyl Sulfones through a Single Electron Transfer Process

作者：Pan Xiao, Chuanfa Ni, Wenjun Miao, Min Zhou, Jingyu Hu, Jingyu Hu, Dingben Chen, Jinbo Hu, Jinbo Hu · 发表于：The Journal of Organic Chemistry · 年份：2019 · DOI：10.1021/acs.joc.9b00419 · 被引用次数：36 · 研究领域：Fluorine in Organic Chemistry、Sulfur-Based Synthesis Techniques、Radical Photochemical Reactions

The fluoroalkylation of various nucleophilic reagents with (phenylsulfonyl)difluoromethyl (PhSO 2 CF 2 )-substituted phenanthridines was achieved to give fluorinated phenanthridine derivatives, which enables the construction of both carbon–heteroatom and carbon–carbon bonds via the substitution of the phenylsulfonyl group. Mechanistic studies indicated that these reactions proceed through a unimolecular radical nucleophilic substitution (S RN 1) mechanism. It is worthwhile noting that in the cases of O-nucleophiles ( t -BuO – and PhO – ), the addition of t -BuOK/PhCHO could significantly promote the reactions, due to the in situ formation of a highly reactive electron donor species through the interaction of t -BuOK, PhCHO, and the solvent DMF, which can effectively initiate the single electron transfer process.