Synthesis of 4-difluoromethylquinolines by NHC-catalyzed umpolung of imines
| Title | Synthesis of 4-difluoromethylquinolines by NHC-catalyzed umpolung of imines |
| Publication Type | Journal Article |
| Year of Publication | 2018 |
| Authors | Patra, A |
| Secondary Authors | Gelat, F |
| Tertiary Authors | Pannecoucke, X |
| Subsidiary Authors | Poisson, T, Besset, T, Biju, AT |
| Journal | Organic Letters |
| Volume | 20 |
| Issue | 4 |
| Pagination | 1086–1089 |
| Date Published | JAN |
| Type of Article | Journal Article |
| ISSN | 15237060 |
| Abstract | The N-heterocyclic carbene (NHC)-catalyzed umpolung of aldimines for the synthesis of 4-difluoromethylquinoline derivatives is reported. In the presence of NHCs, the intramolecular cyclization of aldimines bearing a moderately electron-poor double bond due to the presence of the −CF3 group likely proceeds via the intermediacy of the aza-Breslow intermediate. The key to the success of this aza-Stetter type transformation is the NHC generated from the bicyclic triazolium salt using DBU as the base. |
| DOI | 10.1021/acs.orglett.7b04055 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 6.579 |
Divison category:
Organic Chemistry