Fluoroalkylation of Various Nucleophiles with Fluoroalkyl Sulfones through a Single Electron Transfer Process
| Autor: | Wenjun Miao, Jingyu Hu, Jinbo Hu, Dingben Chen, Pan Xiao, Min Zhou, Chuanfa Ni |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Substitution reaction
Radical-nucleophilic aromatic substitution Phenanthridine 010405 organic chemistry Trifluoromethylation Organic Chemistry Electron donor 010402 general chemistry Organofluorine chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Nucleophile Nucleophilic substitution |
| Zdroj: | The Journal of organic chemistry. 84(13) |
| ISSN: | 1520-6904 |
| Popis: | The fluoroalkylation of various nucleophilic reagents with (phenylsulfonyl)difluoromethyl (PhSO2CF2)-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 (SRN1) 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|