Fluoroalkylation of porphyrins: synthesis and reactions of beta-fluoroalkyltetraarylporphyrins
Jin, LM; Zeng, Z; Guo, CC; Chen, QY
| HERO ID | 4923664 |
|---|---|
| In Press | No |
| Year | 2003 |
| Title | Fluoroalkylation of porphyrins: synthesis and reactions of beta-fluoroalkyltetraarylporphyrins |
| Authors | Jin, LM; Zeng, Z; Guo, CC; Chen, QY |
| Journal | Journal of Organic Chemistry |
| Volume | 68 |
| Issue | 10 |
| Page Numbers | 3912-3917 |
| Abstract | Treatment of 5,10,15,20-tetraarylporphyrins (1) with perfluoroalkyl iodides (2) in the presence of Na(2)S(2)O(4)/NaHCO(3) in DMSO-CH(2)Cl(2) at 30-40 degrees C for several hours gives the corresponding 2-perfluoroalkylporphyrins (3). Nucleophilic attack on 3 with dimethyl malonate, diethyl malonate, malonitrile, or cyano acetate (Nu) anion results in the formation of (E)-3-Nu-2-perfuoroalkyl(methylenyl)chlorins. Electrophilic substitution on 3 with NBS or NO(2) affords regioselectively the corresponding 12(or 13)-bromo- and 12,13-dibromo- or nitroporphyrins. |
| Doi | 10.1021/jo0207269 |
| Pmid | 12737571 |
| Wosid | WOS:000182825000022 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |