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External oxidant-free cross-coupling: electrochemically induced aromatic C-H phosphonation of azoles with dialkyl-H-phosphonates under silver catalysis.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Yurko, E. I. Gryaznova, Tatyana Kholin, Kirill V. Khrizanforova, Vera V. Budnikova, Yulia H. |
| Copyright Year | 2017 |
| Abstract | A convenient external oxidant-free method of phosphorylation of azole derivatives (benzo-1,3-azoles, 3-methylindole, 4-methyl-2-acetylthiazole) by using dialkyl-H-phosphonates through the catalytic oxidation of their mixture under electrochemical mild conditions (room temperature, normal pressure) in the presence of silver salts or oxide (1%) is proposed. This method allows us to obtain the desired azole dialkylphosphonates with good yield (up to 75%). The transformations of silver and phosphorus precursors and intermediates using cyclic voltammetry, ESR, and NMR spectroscopy were investigated, and a radical process mechanism was proposed. It has been found that AgP(O)(OEt)2 is oxidized earlier than other components of the reaction mixture with the elimination of a radical. The ESR spectrum of this radical's adduct was obtained in the presence of the radical trap PBN. Ag2+ is out of the catalytic cycle. |
| Starting Page | 190 |
| Ending Page | 196 |
| Page Count | 7 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/c7dt03650g |
| Alternate Webpage(s) | http://pubs.rsc.org/en/content/articlepdf/2018/dt/c7dt03650g |
| PubMed reference number | 29192918 |
| Alternate Webpage(s) | https://doi.org/10.1039/c7dt03650g |
| Journal | Medline |
| Volume Number | 47 |
| Issue Number | 1 |
| Journal | Dalton transactions |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
