Photocatalytic Systems with Flavinium Salts: From Photolyase Models to Synthetic Tool for Cyclobutane Ring Opening
Hartman, T; Cibulka, R
| HERO ID | 5415151 |
|---|---|
| In Press | No |
| Year | 2016 |
| Title | Photocatalytic Systems with Flavinium Salts: From Photolyase Models to Synthetic Tool for Cyclobutane Ring Opening |
| Authors | Hartman, T; Cibulka, R |
| Journal | Organic Letters |
| Volume | 18 |
| Issue | 15 |
| Page Numbers | 3710-3713 |
| Abstract | Two new photocatalytic systems based on flavinium species formed in situ by protonation of riboflavin-tetraacetate (1) with triflic acid or prepared in advance via alloxazine quaternization are presented as effective tools for oxidative cyclobutane ring [2 + 2] cycloreversion using visible light. The system with 1,3-dimethyl-8-trifluoromethylalloxazinium perchlorate (2c) was found to be superior allowing an acid-free mild procedure, which results in the opening of cyclobutanes with high oxidation potential (up to 2.14 V) and/or with sensitive groups (e.g., furan) without side reactions. |
| Doi | 10.1021/acs.orglett.6b01743 |
| Pmid | 27415962 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |